Find a Maryland fall festival to attend in 2021. Our events calendar for September, October and November 2021 has things to do across Maryland including activities in Baltimore, Frederick, the Eastern Shore, and Aberdeen. Our list includes festivals celebrating the local harvest, food, music, beer, Oktoberfest and more.
At this point we have checked for 2020 dates on all events. Some websites were still holding off on releasing a date, whereas other websites had not been updated at all for this year.
All events showing 2020 dates need to be verified to confirm that changes to the schedule were not made by the organizers after publication here, due to COVID-19. We do not run these events, and would hate for anyone to go out of their way only to find the event had been canceled after releasing a date. Please click through to the event website to confirm! Be safe and have a great fall!
Catoctin Colorfest - Thurmont, MD - Jan 1 to Oct 13, 2019
Canceled for 2020, look for their return in 2021. Normally: Arts & Crafts show featuring 300 well known and respected artists from across the US. One of the largest outdoor craft shows on the East Coast is held as the area’s vibrant leaves are changing.
Bethesda Row Arts Festival - Bethesda, MD - Jan 1 to Oct 11, 2020
Canceled for 2020, look for their return in 2021. Normally: Bethesda Row’s Arts and Entertainment District is transformed into an outdoor art gallery, featuring more than 200 juried fine arts and crafts from artists around the nation.
Heritage Harvest Festival at Soleado Lavender Farm - Dickerson, MD - Jan 1 to Oct 6, 2019
Canceled for 2020, look for their return in 2021. Normally: Free two day, annual event hosted by Heritage Montgomery showcases artisanal farms
Darlington Apple Festival - Darlington, MD - Jan 1 to Oct 5, 2019
Canceled for 2020, look for their return in 2021. Normally: One day crafts festival in the small town of Darlington, Harford County. Festival celebrates all things “apple,”offering entertainment, art, country market, refreshments, and much more
Brunswick Railroad Days - Brunswick, MD - Jan 1 to Oct 4, 2020
Canceled for 2020, look for their return in 2021. Normally: A unique festival that celebrates the city’s railroad heritage as one of the largest rail yards in the nation. Visit the Brunswick Railroad Museum, enjoy entertainment, food and, of course, trains.
Calvert County Watermen’s Festival - Solomon, MD - Jan 1 to Sep 15, 2019
Canceled for 2020, look for their return in 2021. Normally: Watch this spectacular event with work boats and charter boats competing in a Boat Docking Contest, while enjoying live entertainment, refreshments for sale and much more
Maryland Steam Historical Society Show - Upperco, MD - Jan 1 to Sep 20, 2020
Canceled for 2020, look for their return with both a spring and fall show for 2021. Normally: Enjoy the display of steam engines, tractors and gas engines, a flea market, antique cars, food, tractor pulls and equipment demonstrations. Free event, open to the public
Crabtoberfest - Cambridge, MD - Jan 1 to Oct 5, 2019
Canceled for 2020, look for their return in 2021. Normally: Food, beer, live music and fun await you! Enjoy the traditional cuisine of both Germany and the Eastern Shore, including steamed crabs, at the Governor’s Hall at Sailwinds Park.
Queen City Film Festival - Cumberland, MD - Apr 1 to Apr 4, 2021
Postponed from fall 2020. Four days of screenings of films from around the world. QCFF categories are: Animation, Appalachian, Cult, Documentary, Horror/SciFi, Kids/Family, LGBT, and Music
National Folk Festival - Salisbury, MD - Sep 10 to Sep 12, 2021
Itinerant folk festival, held this year in Salisbury. One of the country’s largest, longest-running celebrations of arts, culture, and heritage offers three days of free fun with over 350 traditional musicians, dancers, craftspeople, and more, plus children’s activities, food and craft brews, dancing, storytelling, parades and more. Since 1934, this festival has celebrated Americans, no matter how long or how recently their families have lived on these shores. Free shuttles from Wicomico Youth & Civic Center to Downtown Salisbury.
The Great Frederick Fair - Frederick, MD - Sep 17 to Sep 25, 2021
Features a carnival midway, nightly grandstand entertainment, and international award winning agricultural exhibits
Twist and Stout Festival - Annapolis, MD - Sep 25, 2021
Beer and wine festival with live music, food trucks and artists working at the Festival
Rocktobierfest - Rockville, MD - Oct 2, 2021
Rocktobierfest features two stages of entertainment, including German and rock music, German food, artisans, kids activities, and beverages for sale by local breweries. This annual event attracts more than 5,000 people to Rockville Town Center
We know that you want current events. But we often don’t have dates for the current year. We leave those events with their link here so that you can look for the new dates yourself. We hope you don’t mind!
Bel Air Oktoberfest - Bel Air, MD - Sep 22, 2018
Oktoberfest Taneytown - Taneytown, MD - Sep 22, 2018
Trinity Evangelical Lutheran Church hosts an Oktoberfest that benefits the Habitat for Humanity of Carroll County, with food, beer, music and vendors.
Handsell Autumn Soiree - Cambridge, MD - Sep 22, 2018
An annual fundraising party for the Nanticoke Historic Preservation Alliance at the Garden of Eden to restore Handsell, a Dorchester County historic site listed on the National Register of Historic Places. This is the only chance to see Garden of Eden, one of the finest 19th century homes in Dorchester County, with Greek Revival details, and located on the Great Choptank River.
Vegan SoulFest - Baltimore, MD - Aug 3, 2019
Lots of exhibitors, guest speakers, live entertainment, cooking demonstrations, and more about the vegan lifestyle will be at Clifton Park. Free to the public – bring your lawn chairs!
St Elizabeth Summer Carnival - Baltimore, MD - Aug 24, 2019
Ride a zipline through Patterson Park, and be entertained with live music, kids zone, beer garden, festival food, games and wheels for all ages, flea market, cornhole.
Western Maryland Craft Beverage Festival - Frostburg, MD - Sep 1, 2019
Annual festival designed to showcase Maryland’s wineries, breweries, and distilleries
Amps & Ales - Annapolis, MD - Sep 7, 2019
Over 50 breweries pouring unlimited tasting of over 100 craft beers. A special event for craft beer enthusiasts and music lovers. Features food concessions. Remember to bring your chair and relax. Held at the Arundel Mills. Formerly Annapolis Craft Beer and Music Festival.
Pawpaw Festival - Rockville, MD - Sep 7, 2019
Meadowside Nature Center will celebrate this delightful native fruit with music, crafts, games, expert advice on pawpaw cultivation, and most importantly a pawpaw tasting station
CrowFest - Kennedyville, MD - Sep 8, 2019
Festival at Crow Vineyard & Winery with live music, vendors, wine, food, tours, grape stomping, games and hayrides.
Chestertown Jazz Festival - Chestertown, MD - Sep 12 to Sep 14, 2019
Jazz performances are held throughout Kent County
Halfway to St Paddy’s Day Party - Dowell, MD - Sep 13, 2019
March is just too far away and who can ever stand to wait?! Authentic Irish food and Irish music. There is no cover charge. Don’t forget to wear green!
Washington Ukrainian Festival - Silver Spring, MD - Sep 13 to Sep 15, 2019
Back for the 17th year, enjoy a celebration of Ukrainian culture through the arts and cuisine. Free parking and free admission
Barnyard Bash - Ijamsville, MD - Sep 14 to Sep 15, 2019
Its the Fall opening at Green Meadows Farm as the petting farm opens for the fall season. They’ll have fun vendors, face painting, mechanical bull riding and more. Admission includes the Bash and their other petting farm fun
Bainbridge Day - Port Deposit, MD - Sep 15, 2019
Take a museum tours, a concert, base training center tours, static displays and more
KID Museum FutureFest - Silver Spring, MD - Sep 15, 2019
Featuring hands-on activities that build skills for the future, cutting-edge innovations, and immersive cultural exhibits.
Calverty County Watermen’s Festival - Solomons, MD - Sep 15, 2019
Watch this spectacular event with work boats and charter boats competing in a Boat Docking Contest, while enjoying live entertainment, refreshments for sale and much more
DogFest - Reisterstown, MD - Sep 21, 2019
The Baltimore Humane Society puts on this one day walk-a-thon. Lots of games, fun, vendors and activities for the family and your pets. You can also meet dogs and cats up for adoption!
GrooveFEST Downtown Music Festival - Cambridge, MD - Sep 21, 2019
Soul, funk, jazz and blues sound out throughout downtown Cambridge.
Dorchester Out of the Darkness Walk - Hurlock, MD - Sep 21, 2019
Suicide prevention starts with us! Walk to fight suicide and raise awareness about mental health. Funds raised by the walk benefit the American Foundation for Suicide Prevention, plus a memorial table to honor loved ones and resource tables both before and after the walk
Maryland Lighthouse Challenge - Havre De Grace, MD - Sep 21 to Sep 22, 2019
This challenge involves visiting 13 Maryland lighthouses, with a souvenir at each one, and a special souvenir if you visit all 11 of the “mandatory” lighthouses! Address is for Concord Point Lighthouse, the first on the clockwise line-up
Homestead Gardens Fall Festival - Davidsonville, MD - Sep 21 to Oct 27, 2019
Annual fall festival, with attractions for everyone. Open Saturdays and Sundays.
Strong City Baltimore Oktoberfest - Baltimore, MD - Sep 28, 2019
Strong City Baltimores 5th annual Oktoberfest celebration from 6 to 9 PM! A benefit for The 29th Street Community Center at Peabody Heights Brewery. An evening of authentic German cuisine, local craft beer, music, a silent auction, games, raffles & more!
Frostoberfest - Frostburg, MD - Sep 28 to Sep 29, 2019
This street festival feature German culture, food, music, and bier gardens. They have a kid zone, local crafts, and more.
Winestock Festival - Rising Sun, MD - Sep 28, 2019
Food, wine & beer, and live music
Old Stein Inn Oktoberfest - Edgewater, MD - Sep 28, 2019
Oktoberfest kickoff party is 6-10 pm with German music on the accordian, food and more. Celebration continues select dates thereafter.
MD Folk Festival - Frederick, MD - Sep 28, 2019
Features the best local folk musicians covering different types of music
RetroFest on the Potomac - Piney Point, MD - Sep 28, 2019
RetroFest on the Potomac represents all things vintage. Admire classic cars, browse for vintage treasures and step back in time to the nostalgic tunes of yesteryear.
Takoma Langley Crossroads Night Market - Takoma Park, MD - Sep 28, 2019
Enjoy the international flavors of the Crossroads. Over twenty vendors including local restaurants and food vendors serving their best dishes. Enjoy craft beer from Silver-Branch Brewery, craft vendors, mainstage performances, kids’ entertainment.
Washington Grove Fall Festival - Washington Grove, MD - Sep 28, 2019
Thirty talented artisans will be showing and selling their beautiful creations on the green in historic Washington Grove. Food trucks, pumpkin patch, pumpkin painting, live music, petting zoo and much more make for terrific Saturday fun
Days End Farm Horse Rescue Fall Festival - Woodbine, MD - Sep 28, 2019
Days End Farm Horse Rescue’s annual Fall Festival features a HOPS for Horses Beer Garden, horse demonstrations, vendors, live music, games, pony rides, face painting, petting zoo, and more
DuckFest - Dowell, MD - Sep 29, 2019
Live music, craft beer, authentic German food
Baltimore Japan Art Festival - Baltimore, MD - Oct 3 to Oct 6, 2019
Annual festival showcasing Japanese culture through art, film, music and food
Multi-Cultural Festival and Oktoberfest - Columbia, MD - Oct 4 to Oct 6, 2019
Oktoberfest with beer garden on Friday night, and multi-cultural festival over the weekend.
Rotary Oktoberfest of Carroll County - Westminster, MD - Oct 5 to Oct 6, 2019
Fundraising event held by the four Rotary Clubs of Carroll County at Danele Shipley Memorial Arena. Enjoy family friendly activities and authentic German food, beer and live music. Plenty of contests including the Lederhosen & Dirndl competition, Chicken Dance contest and Polka Dance contest. There will be pumpkin painting, scarecrow making, face painting, magic shows, games and balloon sculpting for kids. Football tent ensures you don’t miss the action over the weekend. General admission is $10, with those wearing authentic German attire and children ages 10 and under free – or save $2 with 5 nonperishable donation for the animal rescue.
ARToberFEST - Stevensville, MD - Oct 5, 2019
Enjoy this celebration of local food, music, artisans and breweries in historic Stevensville.
Halloween at the Vineyards - Parkton, MD - Oct 5, 2019
Celebrate Halloween at the Royal Rabbit Vineyards. Come in costume for a costume contest
Prince Georges Fall Fest - Bowie, MD - Oct 5, 2019
Complimentary wine tastings, food vendors, exhibitors and artisans, music and other entertainment! Former fundraiser was an Oktoberfest
Taste of Bethesda - Bethesda, MD - Oct 5, 2019
Taste of Bethesda returns and will bring nearly 50 restaurants and multiple stages with music and cultural entertainment and kid’s corner. Admission to Taste of Bethesda is free. Tickets will be sold on-site for food, tickets are $5 for 4 tickets
Oakland Mills Fall Festival - Columbia, MD - Oct 5, 2019
Free admission to this festival held rain or shine
Frederick Fall Festival - Frederick, MD - Oct 5 to Oct 6, 2019
Celebrate local agricultural heritage. Sat. morning tractor pull; Sun. afternoon cake auction and kiddie pedal pull. Hayrides, farm exhibits, demos, animals, food, & crafts. Hands-on crafts, games, & candle-dipping
Riverside WineFest at Sotterley - Hollywood, MD - Oct 5 to Oct 6, 2019
Enjoy Maryland wines at this National Historic Landmark
Hurlock Fall Festival and Train Rides - Hurlock, MD - Oct 5, 2019
The parade kicks off on Main St at 10am; train rides from Hurlock to Federalsburg leave the station on Gay Street at 11am, 12:30pm, 2, 3:30 and 5pm ($8 Round Trip). Enjoy food, music, fishmobile, bubble show, zoo to you, scales & tales display, pony rides, more
Heritage Harvest Festival - Poolesville, MD - Oct 5 to Oct 6, 2019
Celebrate the fall harvest in the Montgomery County Agricultural Reserve. Visit a variety of farms with fun family activities including farm tours, markets, crafts for kids, farm animals, historic structures, and food for sale
Olde Mother Brewing Oktoberfest - Frederick, MD - Oct 6, 2019
Tickets include: Custom branded commemorative mug, 2 beer tokens for 20 oz mug pours, Weisswurst and Bavarian Bratwurst (shipped from Germany), German potato salad and homemade beer mustard all by the great Chef Niko at Roast House Pub! PLUS $4 festbier refills all day! Traditional German music by the Edelweiss Band. *10 oz Bavarian pretzels available for purchase separately*
Grape Harvest Festival - Thurmont, MD - Oct 12, 2019
Tours of a harvest-season winery (this year is Layton’s Chance Vineyard & Winery), with a lesson on how grapes are processed, what wine making equipment is used, and how the harvest process goes. Live music and pizza too!
Joppatowne Arts Festival - Joppa, MD - Oct 12, 2019
Handmade arts and crafts, food trucks, and live music. Rain or shine, This event was formerly known as the Waterfront Arts and Crafts
Fairyfest at Adkins Arboretum - Ridgely, MD - Oct 12, 2019
Bring your wings for a day of magic. Follow a trail of fairy houses along enchanted forest paths, hunt for gnomes in the Funshine Garden, and join in a meadow maypole dance. Natural materials will be on hand for making an array of magical crafts.
Italian Food and Wine Festival - St Michaels, MD - Oct 12, 2019
The 10th Annual Italian Wine & Food Festival takes place over Columbus weekend under tents at Simpatico, Italy’s Finest. Taste over 70 different Italian wines and limoncellos, enjoy fabulous Italian food, music and more
Nanticoke River Jamboree - Vienna, MD - Oct 12, 2019
The staff at Handsell are pleased to join in the celebration of the countys 350th Anniversary, giving them a wide range for interpreting the history of Handsell from the Native People to the African American enslaved and sharecroppers and including colonial settlement. Through historic craftspeople, docents in period dress, open hearth cooking demonstration by African American interpreters , Native life skills and the history of the Eastern Shore waterways, visitors can immerse themselves in over 350 years of history.
Annapolis Harvest Beer Festival - Annapolis, MD - Oct 13, 2019
Local Breweries show off their harvest craft brews in the heart of Annapolis. Beer, food, music
Hancock’s Resolution Fall Harvest Festival - Pasadena, MD - Oct 13, 2019
Bring the family and build a scarecrow, bob for apples, and make cornmeal, plus folk music and harvest dinner.
Bark in the Park Talbot County - Easton, MD - Oct 13, 2019
The annual Bark in the Park forTalbot Humane features a timed 5K fun run-walk, Dog Show, K9 demos, kids activities, delicious food, live music, games, local artisans and much more.
Russian Festival - Baltimore, MD - Oct 18 to Oct 20, 2019
Savor the authentic foods, prepared by the parishioners, browse the import kiosk, visit the children’s corner, and enjoy the dance groups and musical ensembles. Plus, tour the historic church to view a structure dating back to the 1860s.
Brews and Bivalves - Laurel, MD - Oct 19, 2019
A day of craft beer, oystersbuck-a-shuck, fried, grilled, and baked, Casino-style and fundraising fun to benefit the Oyster Recover Partnership. Plus, new beer releases, live music, local ice cream (made with Jailbreak Brewery beer), and more.
Garden Glow at Ladew Gardens - Monkton, MD - Oct 19 to Oct 20, 2019
Unique celebration of fall featuring illuminated sculptures, hundreds of glowing jack o lanterns, live music, and food & spirits. Garden Glow also features educational programs including animal presentations!
Harvest at the Hill Festival - Ellicott City, MD - Oct 19, 2019
Manor Hill Farm is hosting their annual Harvest at the Hill Festival on their 54-acre farm in Ellicott City. Featuring Manor Hill beer, live music, food trucks, yard games, and farm fun!
Hops 2 Grapes Craft Beer, Wine and Whiskey Festival - Bel Air, MD - Oct 19, 2019
Enjoy craft beer, local and international wines, whiskey, morning yoga, live music and food trucks. Enjoy a 165 acre farm in rural Bel Air, MD, and experience the best Maryland has to offer.
Tilghman Island Day - Tilghman, MD - Oct 19, 2019
Arts and nautical crafts, boat building demonstrations, oyster shucking, crab picking and a look at the life of a waterman. The watermen’s boat docking contest is always a highlight
Wine on the Water at Kurtz’ Beach - Pasadena, MD - Oct 19 to Oct 20, 2019
Spend the weekend at Kurtz’s Beach in Pasadena for the fifth-annual Wine On The Water, an all-encompassing festival that features a variety of vendors, musicians and attractions.
Elkridge Fall Festival - Elkridge, MD - Oct 20, 2019
A Maryland Artisan Market and Festival that will take place at the historic Elkridge Furnace Inn on the Garden House grounds. This rain or shine festival will also feature live music and food celebrating all things Maryland
Maryland Good Sam Fall Rally - Frederick, MD - Oct 25 to Oct 27, 2019
Activities include a theme parade, ice cream social, parade of flags, games and crafts, and even bingo (aka samgo).
Shore Craft Beer Fest – Octoberfest - Ocean City, MD - Oct 26, 2019
Experience a craft beer festival featuring only local craft beers brewed on the Shore while enjoying the beauty of Ocean City in the off-season
Witches and Wizards Weekend - Baltimore, MD - Oct 26 to Oct 27, 2019
Over this weekend young witches and wizards are encouraged to delve into a world of sorcery and witchcraft, dress as their favorite witch or wizard, learn how to make edible potions, make wands and more
Baltimore Book Festival - Baltimore, MD - Nov 1 to Nov 10, 2019
A celebrations of books, with demonstrations, readings, stage shows and more.
Augustoberfest - Hagerstown, MD - Aug 15 to Aug 16, 2020
This annual Oktoberfest pays tribute to the area’s rich German heritage and supports exchange students from its sister city in Wiesel, Germany. Tickets are $5.
Maryland State Fair - Lutherville-Timonium, MD - Aug 27 to Sep 7, 2020
An annual state fair held at Maryland State Fairgrounds. Enjoy carnival rides, thoroughbred horseracing, livestock shows, 4H/FFA exhibits, kiddie rides, and great carnival style food. Since 1878.
Maryland Renaissance Festival - Annapolis, MD - Aug 29 to Oct 25, 2020
Weekends through October, come celebrate the past at Revel Grove
National Hard Crab Derby - Crisfield, MD - Aug 31 to Sep 6, 2020
Features live entertainment, music, parade, fireworks, carnival rides, beauty pageant, races, contests and lots of family fun with crafts, arts, and more vendors. Famous for the crustacean race from which it gets its name
Deep Creek Lake Art & Wine Festival - McHenry, MD - Sep 12, 2020
Arts festival features beautifully handcrafted works by local and regional artisans, more than 200 wines from local and national wineries, live entertainment, food, wine pairing dinners and more. Benefits HART for Animals and Garrett Lakes Arts Festival.
In the Street Festival - Frederick, MD - Sep 12, 2020
Over 30 years downtown Frederick has hosted this event on Market Street. Lots of food, fun, entertainment for over 75,000 festival goers.
Reisterstown Festival - Reisterstown, MD - Sep 12 to Sep 13, 2020
Watch the parade, enjoy the Beer Garden, listen to lots of live music, with plenty of family and kids fun, foods, drinks, crafts, arts, and more.
Baltimore Rhythm Festival - Baltimore, MD - Sep 12, 2020
The musical event is moving virtual for 2020 – check out details on the event’s website. Normally: Celebrates rhythm in its many forms in an event dedicated to “Peace Through Music” and features performances, workshops, vendors, and jam sessions
OC Bikefest - Ocean City , MD - Sep 16 to Sep 20, 2020
Vendors, merchandise, food, concerts & entertainment!
Anne Arundel County Fair - Crownsville, MD - Sep 16 to Sep 20, 2020
Enjoy the farm animals, exhibits, contests, carnival midway, entertainment, family atmosphere, agriculture education, 4-H exhibits and auction at this traditional county fair.
Charles County Fair - La Plata, MD - Sep 17 to Sep 1, 2020
Exhibits as varied as livestock, arts and crafts, great entertainment, special events and activities for all ages including pig races, carnival and pony rides
Harford Plein Air Festival - Bel Air, MD - Sep 18 to Nov 20, 2020
The Harford Plein Air Festival is an annual juried plein air painting competition and art sale in Harford County hosted by the Maryland Center for the Arts. Artists from all over the U.S. apply to be accepted into the festival.
Worcester County Fair - Snow Hill, MD - Sep 18 to Sep 20, 2020
Attend a traditional county 4-H fair with livestock, a horse show, live entertainment and craft and food vendors
Autumn Wine Festival - Salisbury, MD - Sep 19 to Sep 20, 2020
Features wine samplings, guided tours of Pemberton Hall, Sports Zone with telecast games and lawn games, and more! Participate in a variety of fundraising opportunities for the Women Supporting Women Partnership, a locally-based nonprofit helping those with breast cancer.
Maryland Wine Festival - Westminster, MD - Sep 19 to Sep 20, 2020
Sample over 150+ Maryland wines, enjoy a juried art show, listen to live music, snack on locally made food and artisanal cheeses, and more! Get a commemorative wine glass with sampling from all participating wineries! There is also a VIP package, and designated drivers get in for a reduced rate. Children under 12 get in free with a paid adult ticket. Held at the Carroll County Farm Museum. There is parking available onsite, plus free handicap-accessible shuttles from Carroll Community College and the Carroll County Office Building.
Native American Festival - Vienna, MD - Sep 19, 2020
The Native American Festival features traditional dancers, singers, drumming, crafts, artists’ demonstrations, authentic Native food, a large silent auction and more. This pow-wow is organized by the Nause Waiwash Band of Indians, made up of descendants of local Nanticoke Indians.
Hispanic Festival - Adelphi, MD - Sep 20, 2020
Celebrate the rich heritage of Hispanic communities and families with entertainment, music, food, games and crafts
Upperco Music Festival - Upperco, MD - Sep 23 to Sep 26, 2020
Bluegrass & traditional country music festival includes camping, craft beer, workshops, vendors, jamming, band competition. Both 4-day and single-day tickets available
Westminster Fall Fest - Westminster, MD - Sep 24 to Sep 27, 2020
Features a parade, fun run, craft vendors, food court and fun in City Park.
High Zero - Baltimore, MD - Sep 24 to Sep 27, 2020
A music festival of live experimental improvised music with lots of performers.
Wine on the Beach - Ocean City, MD - Sep 25 to Sep 26, 2020
Head to the Inlet, where wine offerings and regional cuisine abound, plus arts and crafts vendors, micro-brews for purchase, live music and more!
APG Oktoberfest - Aberdeen Proving Ground, MD - Sep 25 to Sep 26, 2020
Held at the Aberdeen Proving Grounds. 11 AM to 9 PM.
Maryland Microbrewery Festival - Westminster, MD - Sep 26, 2020
An annual event at Union Mills Homestead. Features continuous live music, entertainment, historic site, ample parking, a variety of breweries and beers, food vendors, craft vendors, and brewing seminars.
Das Best Oktoberfest - Baltimore, MD - Sep 26, 2020
Kick off beer week with this all you can taste Baltimore Oktoberfest. 60,000+ generally attend this annual event. VIP admission starts at noon and regular admission is from 2 PM to 6 PM. Over 150 local, domestic and international beers, wines and schnapps. German food, including sausages, available for purchase ala carte. Authentic polka and oompah bands, chicken dancing and live music from regional bands. Contests offering cash prizes include the Miss Oktoberfest competition and the Best Beer Belly contest. Limited parking is available for $10 per car. Wear your German outfit and, while supplies last, you will get a free beer lanyard. Regular admission tickets are $40 in advance. This provides you admission to the event, souvenir tasting glass and unlimited beer sampling. VIP admission offers access to special beer tastings, 2 extra hours of drinking and restaurant sampling, opening tap celebration, VIP washrooms and parking pass. Designated driver tickets are $25 or $39 (for VIP). Kids 12 and under are free but not recommended. Location: M & T Stadium Parking Lot, Baltimore, Maryland. A portion of ticket sales go to The Spirit of Hope Children’s Foundation.
Fall Harvest and Craft Festival - Havre de Grace, MD - Sep 26 to Sep 27, 2020
Enjoy Harford County’s original Fall festival with apple cider pressing & butter making, pumpkin painting and scarecrow making and hayrides, craft vendors and demonstrations of historical trade, live bluegrass music, food and kids’ activities.
Six Flags America Fright Fest - Upper Marlboro, MD - Sep 26 to Nov 1, 2020
Enjoy the spookiness of Thrills by Day and Fright by Night. There is no “leisurely stroll” during Fright Fest. And terror isn’t confined to haunted attractions. Weekends only.
Maryland Seafood Festival - Annapolis, MD - Sep 26 to Sep 27, 2020
Open rain or shine, the festival features live toe-tapping music, kids fun, vendors arts and crafts, great food and drink, cooking demonstrations, and lots of contests.
Calvert County Fair - Prince Frederick, MD - Sep 30 to Oct 4, 2020
Calvert County’s long agricultural heritage and history is celebrated yearly with an old-fashioned county fair. See farm animals, displays of all kinds, demonstrations and delicious Southern Maryland cooking
Chesapeake Film Festival - Easton, MD - Oct 1 to Oct 4, 2020
The annual program focuses on stories about the Maryland region and local communities
Sunfest - Ocean City, MD - Oct 1 to Oct 4, 2020
Free admission to this event that features great food, live music, hayrides, and lots of fun things to do. ;Held at the inlet lot on the south end of the boardwalk.
Charm City Fringe Festival - Baltimore, MD - Oct 1 to Oct 10, 2020
The annual Charm City Fringe, Baltimore’s 11-day festival of experimental theater and performance art, returns to the Bromo Arts District with more than 90 performances by artists from all over North America
Frederick’s Oktoberfest - Frederick, MD - Oct 2 to Oct 3, 2020
Oktoberfest bier, bratwurst, dancing, live music and children’s activities to benefit Frederick County charities and local organizations. Hosted at the Frederick Fairgrounds. Friday is 21+ only.
Mid-Atlantic Small Craft Festival - St Michaels, MD - Oct 2 to Oct 3, 2020
Small craft, big fun. Join small boat enthusiasts and unique watercraft
Artisans Festival at Wye Mills - Wye Mills, MD - Oct 3, 2020
Enjoy and explore the many art forms on display including paintings, pottery, jewelry, photography, prints, fiber arts and so much more
Harvest Festival at Agricultural History Farm Park - Derwood, MD - Oct 3, 2020
Enjoy some down-home fun on the farm with old-time crafts, activities, music, and food. Montgomery Parks Agricultural History Farm Park is situated on 455 acres of land and serves as a historic farm site as well as a modern farming activity center
Bowie International Festival - Bowie, MD - Oct 3, 2020
Travel around the world in a day. Enjoy international foods, music, dance performers, international bands and more. Free admission!
Anne Arundel Craft Show - Crownsville, MD - Oct 3 to Oct 4, 2020
Hundreds of local artists with handcrafted goods, at the Anne Arundel Fairgrounds
Maryland Pumpkin Festival - Frederick, MD - Oct 3 to Oct 4, 2020
Annual event with a corn maze, hay slides, farm animals, pumpkin patch, pig races, live music and of course a great pumpkin patch. Also has a Pumpkin Princess Storytime, pumpkin hunt, candy shoot, and some painting and sculpturing demonstrations.
Takoma Park Street Festival - Takoma, MD - Oct 4, 2020
Features local artists, and crafters who offer paintings, pottery, silk-screening, stained glass, woodworking, textiles and ceramics along with plenty of food trucks.
Autumn Glory Festival - Oakland, MD - Oct 7 to Oct 11, 2020
An annual event with two large parades, live music concerts, band competitions, art exhibits, craft shows and of course plenty of foods. Come celebrate the beauty of fall foliage, now running for over 50 years!
Endless Summer Cruisin’ - Ocean City, MD - Oct 8 to Oct 11, 2020
Massive car show with over 2000 hot rods, custom cars, trucks and more, plus vendors
Good Beer Festival - Salisbury, MD - Oct 9 to Oct 10, 2020
Over 100 different craft beers and unlimited tastings from master brewers. Features include a live music line-up, and the Sports Zone with telecasts of the biggest games of the weekend. Held at the Pemberton Historical Park.
Sugarloaf Crafts Festival – Timonium - Timonium-Lutherville, MD - Oct 9 to Oct 11, 2020
Explore artist and crafter booths at the Maryland State Fairgrounds for a weekend of artistic appreciation and entertainment for all.
Fells Point Fun Festival - Baltimore, MD - Oct 10 to Oct 11, 2020
Over 10 bands perform in live stage entertainment. Lots of family fun, vendors of arts and crafts, kids activities, food, drinks, and more. Admission is free – reserve some parking nearby and walk into this festival. This festival has been running for over 50 years!
Havre de Grace Oktoberfest - Havre de Grace, MD - Oct 10, 2020
Free admission. A family friendly event with German beer/wine and German entertainment.
Fall Fest with Oysters - Rock Hill, MD - Oct 10, 2020
A celebration of family, community and oysters. Enjoy music, crafts, food and fun on Main Street in Rock Hall which includes a kids’ court and more, rain or shine
Autumn Reggae Wine and Music Festival - Mt Airy, MD - Oct 10 to Oct 11, 2020
Enjoy your favorite Linganore Wines while relaxing and listening to live bands, sampling authentic island cuisine, and hand-crafted artisan goods.
Hops and Harvest Festival - Columbia, MD - Oct 10, 2020
Showcases the finest craft beer, music, and food.
Oktoberfest at the Kentlands - Gaithersburg, MD - Oct 11, 2020
Wine-tasting featuring local Maryland vineyards and retailers, a traditional Beer Garden, food vendors and German entertainment. Live entertainment, artists and crafters, free horse-drawn wagon rides, apple cider pressing, traditional Oktoberfest crafts for children, and nonprofit vendors. Along Main Street, there are four more stages of entertainment featuring variety bands and community groups, an extended business expo, strolling entertainers, mini golf, children’s crafts, inflatables, and plenty of restaurants and retail establishments to explore. Noon to 5 PM. Admission and parking are free.. Satellite parking at 101 Orchard Ridge Drive
La Plata Fall Festival - La Plata, MD - Oct 11, 2020
Live music, petting zoo, train rides, craft and food vendors and fun for all!
Baltimore Running Festival - Baltimore, MD - Oct 17, 2020
Over 5 distance options for runners of all abilities, with the finishing line at the Inner Harbor, plus an UnderArmour shirt for all participants!
U.S. Oyster Festival, Maryland - Leonardtown, MD - Oct 17 to Oct 18, 2020
An annual festival at St. Mary’s County Fairgrounds. Lots of great food and oysters cooked in many different and unique ways. Also live entertainment, demonstrations, and fun for over 50 years.
Berlin Octoberfest - Berlin, MD - Oct 17, 2020
Music, german food, craft vendors, annual Fall sidewalk sale, beer garden, games and activities such as face painting, scarecrow making, pumpkin painting and others for the kids. Annual cornhole tournament at Burley Tavern. Free parking at Berlin Intermediate School with shuttle to downtown.
Oktoberfest at Schifferstadt - Frederick, MD - Oct 17 to Oct 18, 2020
Annual event on the third weekend in October. Free admission. Hours are 11 to 6 pm on Saturday and noon to 5 pm on Sunday. Enjoy the great food, lively German music, historic demonstrators, and hand-made products from many art and craft vendors hosted by the Frederick County Landmarks Foundation at the Schifferstadt Architectural Museum.
Berlin Oktoberfest - Berlin, MD - Oct 17, 2020
Music, food, annual fall sidewalk sale, beer garden, games and activities, including the cornhole tournament. Free shuttle is available.
American Indian Festival at Patuxent River Park - Upper Marlboro, MD - Oct 17, 2020
Celebrate Native American Indian culture and heritage with live traditional music, dancing, storytelling, archery, exhibits and crafts.
Sailwinds Park East Kite Festival - Cambridge, MD - Oct 18, 2020
Free festival features kites of all shapes and sizes. Bring your own kite, buy one, or watch expert kite flyers, plus bungee bounce, face painting, food, music and more
Silver Spring Arts and Crafts Fall Fair - Silver Spring, MD - Oct 18, 2020
Come start your holiday shopping early with arts & crafts vendors.
Greek Food, Wine and Culture Festival - Baltimore, MD - Oct 22 to Oct 25, 2020
The annual Annunciation Cathedral food, wine & culture festival returns with dance, live music, pastries, food, wine along with cathedral tours and shopping opportunities.
Baltimore Comic Con - Baltimore, MD - Oct 23 to Oct 25, 2020
Considered “America’s Greatest Comic Book Convention” is held annually Labor Day weekend at the Baltimore Convention Center.
BARCStoberfest - Baltimore, MD - Oct 23 to Oct 25, 2020
BARCStoberfest returns with the super popular beer garden, shopping, yoga class, kids scavenger hunt, and the Ready Set Sniff! 5K or 1 Mile walk through Patterson Park
OC-Toberfest - Ocean City, MD - Oct 24 to Oct 25, 2020
A celebration of October and Halloween with a beach maze, pet parade, Great Pumpkin Race and Halloween costume party for kids. Events vary by day.
Silver Springs Holiday Crafts, Desserts and Sweets Festival - Silver Spring, MD - Oct 25, 2020
Get the little ones ready for Halloween. Dress them up and bring them for the Costume Parade while they enjoy all the sweets and you enjoy the arts and crafts.
OysterFest at Chesapeake Bay Maritime Museum - St Michaels, MD - Oct 31, 2020
Celebrate the Chesapeake oyster featuring Sip, Slurp, & Savor! Live music, boat rides, retriever demos, oysters and local fare, oyster stew competition, cooking demos, childrens activities. Rain or shine.
Maryland Irish Festival - Timonium, MD - Nov 13 to Nov 15, 2020
A cultural event with workshops, demonstrations, traditional food, Irish Dancers, live music, food, beer, and arts and crafts.
Sugarloaf Crafts Festival – Gaithersburg - Gaithersburg, MD - Nov 20 to Nov 22, 2020
Explore artist and crafter booths at the Montgomery County Fairgrounds for a weekend of artistic appreciation and entertainment for all.
Find other fun things to do in Maryland in the fall: