Fall Maryland Festivals

Find a Maryland fall festival to attend in 2019. Our events calendar for September, October and November 2019 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.

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Aberdeen Fall FestivalsBaltimore Fall FestivalsEastern Shore Fall FestivalsFrederick Fall Festivals

2019 Festivals

Maryland State Fair - Lutherville-Timonium, MD - Aug 22 to Sep 2, 2019
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 Wine Festival - Westminster, MD - Sep 21 to Sep 22, 2019
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.  

Das Best Oktoberfest - Baltimore, MD - Sep 28, 2019
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.

Past Events

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!

Oktoberplex - Boyds, MD - Oct 2, 2016

Oktoberfest at the Kentlands - Gaithersburg, MD - Oct 9, 2016
Wine-tasting featuring local Maryland vineyards and retailers, a traditional Beer Garden, food vendors and German entertainment. A cappella performance groups, 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 200 Orchard Ridge Drive, just off of Quince Orchard Road.

Steppingstein - Havre de Grace, MD - Oct 21, 2016
A refined Oktoberfest celebration and fundraiser for Steppingstone. Authentic german dinner, beer/wine tasting and group polka lessons.

Old Stein Inn Oktoberfest - Edgewater, MD - Sep 15, 2017
Oktoberfest Kickoff Party is 6-10 PM. Celebration continues thereafter.

Annapolis Craft Beer and Music Festival - Annapolis, MD - Sep 16, 2017
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 Navy-Marine Corps Memorial Stadium.

Maryland Lighthouse Challenge - Havre De Grace, MD - Sep 16 to Sep 17, 2017
This challenge involves visiting 10 Maryland lighthouses, with a souvenir at each one, and a special souvenir if you visit all 10! Address is for Concord Point Lighthouse, the first on the clockwise line-up

Taste of Heaven Caterers Oktoberfest - Baltimore, MD - Oct 13, 2017
Held at Delta Community Center.

Prince Georges Oktoberfest - Bowie, MD - Oct 14, 2017

Augustoberfest - Hagerstown, MD - Aug 18 to Aug 19, 2018
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.

Vegan SoulFest - Baltimore, MD - Aug 25, 2018
Lots of exhibitors, guest speakers, live entertainment, cooking demonstrations, and more about the vegan lifestyle will be at Clifton Park.

National Hard Crab Derby - Crisfield, MD - Aug 27 to Sep 2, 2018
Features live entertainment, music, parade, fireworks, carnival rides, beauty pageant, races, contests and lots of family fun with crafts, arts, and more vendors.

National Folk Festival - Salisbury, MD - Sep 7 to Sep 9, 2018
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.

Grape Harvest Festival - Thurmont, MD - Sep 7, 2018
Tours of a harvest-season winery, with a lesson on how grapes are processed, what wine making equipment is used, and how the harvest process goes at Catoctin Breeze. Live music and pizza too!

Deep Creek Lake Art & Wine Festival - McHenry, MD - Sep 8, 2018
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 8, 2018
Over 25 years downtown Frederick has hosted this event on Market Street.  Lots of food, fun, entertainment for over 70,000 festival goers.

Maryland Seafood Festival - Annapolis, MD - Sep 8 to Sep 9, 2018
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.

Reisterstown Festival - Reisterstown, MD - Sep 8 to Sep 9, 2018
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.

CrowFest - Kennedyville, MD - Sep 9, 2018
Festival at Crow Vineyard & Winery with live music, vendors, wine, food, tours, grape stomping, games and hayrides.

High Zero - Baltimore, MD - Sep 14 to Sep 29, 2018
20th annual. A music festival of live experimental improvised music with lots of performers. Held in three cities (Chicago, New York City, and Baltimore)

DogFest - Reisterstown, MD - Sep 15, 2018
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!

APG Oktoberfest - Aberdeen Proving Ground, MD - Sep 15, 2018
Held at the Aberdeen Proving Grounds. 11 AM to 9 PM.

Native American Festival - Vienna, MD - Sep 15 to Sep 16, 2018
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.

GrooveFEST: Blues, Brews & BBQ - Cambridge, MD - Sep 15, 2018
Soul, funk, jazz and blues sound out throughout downtown Cambridge while attendees enjoy bbq and beers. Admission to the street festival is free however there are sections that may require ticketed admission.

Sunfest - Ocean City, MD - Sep 20 to Sep 23, 2018
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.

Dorchester Out of the Darkness Walk - Hurlock, MD - Sep 22, 2018
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

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.

Homestead Gardens Fall Festival - Davidsonville, MD - Sep 22 to Oct 28, 2018
35th annual fall festival, with attractions for everyone. Open Saturdays and Sundays.

Westminster Fall Fest - Westminster, MD - Sep 27 to Sep 30, 2018
40th annual!  Features a parade, fun run, craft vendors, food court and fun in City Park.

Baltimore Book Festival - Baltimore, MD - Sep 28 to Sep 30, 2018
A full weekend of books, demonstrations, readings, stage shows and more.

Baltimore Comic Con - Baltimore, MD - Sep 28 to Sep 30, 2018
Considered “America’s Greatest Comic Book Convention” is held annually Labor Day weekend at the Baltimore Convention Center.

Frederick’s Oktoberfest - Frederick, MD - Sep 28 to Sep 29, 2018
Oktoberfest bier, bratwurst, dancing, live music and children’s activities to benefit Frederick County charities and local organizations. Hosted at the Frederick Fairgrounds.

Wine on the Beach - Ocean City, MD - Sep 28 to Sep 29, 2018
Head to the Inlet, where wine offerings and regional cuisine abound, plus arts and crafts vendors, micro-brews for purchase, live music and more!

Maryland Microbrewery Festival - Westminster, MD - Sep 29, 2018
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.

Your Wish My Dish Catering Oktoberfest - Baltimore, MD - Sep 29, 2018

Winestock Festival - Rising Sun, MD - Sep 29, 2018
Food, wine & beer, and live music

DuckFest - Dowell, MD - Sep 30, 2018
Live music, craft beer, authentic German food

Endless Summer Cruisin’ - Ocean City, MD - Oct 4 to Oct 7, 2018
Massive car show with over 2000 hot rods, custom cars, trucks and more, plus vendors

Rotary Oktoberfest of Carroll County - Westminster, MD - Oct 6 to Oct 7, 2018
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 $5, with those wearing authentic German attire and children ages 10 and under free.

Strut Your Mutt DC Metro - Silver Spring, MD - Oct 6, 2018
Strut Your Mutt is a fun dog walk and fundraising event that raises money to help save the lives of homeless pets, supporting your choice of one of hundreds of participating shelters, rescue groups, and other animal welfare groups. There are Strut your Mutt events across the country.

Frostoberfest - Frostburg, MD - Oct 6, 2018
This street festival feature German culture, food, music, and bier gardens. They have a kid zone, local crafts, and more.

Maryland Pumpkin Festival - Frederick, MD - Oct 6 to Oct 7, 2018
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.

Taste of Bethesda - Bethesda, MD - Oct 6, 2018
Over 60 restaurants and lots of live music across five stages make this one of most popular festival with over 40,000 in annual attendance. Also kids area and arts, crafts, great food and more. Free admission with tasting tickets sold on site.

Crabtoberfest - Cambridge, MD - Oct 6 to Oct 16, 2018
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. Open from 3 to 9 PM. General admission is $10.

Takoma Park Street Festival - Takoma, MD - Oct 7, 2018
 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 10 to Oct 14, 2018
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!

Chesapeake Film Festival - Easton, MD - Oct 11 to Oct 14, 2018
The 11th annual program is focusing on stories about the Maryland region and local communities

Good Beer Festival - Salisbury, MD - Oct 12 to Oct 13, 2018
Over 100 different craft beers and unlimited tastings from master brewers. Â Features include a live music line-up, and the Sports Zone with telecasts of the biggest games of the weekend. Â Held at the Pemberton Historical Park.

Sugarloaf Crafts Festival – Timonium - Timonium-Lutherville, MD - Oct 12 to Oct 14, 2018
Explore artist and crafter booths at the Maryland State Fairgrounds for a weekend of artistic appreciation and entertainment for all.

Baltimore Beer Week - Baltimore, MD - Oct 12 to Oct 21, 2018
10th annual. A collaborative effort of businesses and beer enthusiasts to celebrate and highlight the unique beer culture that exists in and around the Chesapeake region. Hundreds of beer-centric events that focus on beer culture, culinary aspects, meet and greets, homebrew demos and even beer history.

Fell’s Point Fun Festival - Baltimore, MD - Oct 13 to Oct 14, 2018
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!

Berlin Octoberfest - Berlin, MD - Oct 13, 2018
Music, german food, craft vendors, annual Fall sidewalk sale. Beer garden by Burley Oak Brewing Company. 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.

Havre de Grace Oktoberfest - Havre de Grace, MD - Oct 13, 2018
Free Admission. A family friendly event with German beer/wine and German entertainment.

Strong City Baltimore Oktoberfest - Baltimore, MD - Oct 13, 2018
Strong City Baltimore’s 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!

La Plata Fall Festival - La Plata, MD - Oct 14, 2018
Live music, petting zoo, train rides, craft and food vendors and all

Baltimore Running Festival - Baltimore, MD - Oct 20, 2018
Over 5 distance options for runners of all abilities, with the finishing line at the Inner Harbor, plus an UnderArmour shirt for all participants!

Hereford Fall Festival - Hereford, MD - Oct 20 to Oct 21, 2018
Enjoy food, crafts, vendors, fine wines, chocolates, live music, monster truck display, and plenty of cold beer.  Over 150 food and craft vendors on display at this event.

Autumn Wine Festival - Salisbury, MD - Oct 20 to Oct 21, 2018
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.

U.S. Oyster Festival, Maryland - Leonardtown, MD - Oct 20 to Oct 21, 2018
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.

Oktoberfest at Schifferstadt - Frederick, MD - Oct 20 to Oct 21, 2018
Annual event on the third weekend in October. Free admission. Hours are 10 to 5 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.

OC-Toberfest - Ocean City, MD - Oct 20 to Oct 28, 2018
A two weekend celebration of October and Halloween with a beach maze, pet parade, Great Pumpkin Race and Halloween costume party for kids. Events vary by day.

Maryland Good Sam Fall Rally - Frederick, MD - Oct 26 to Oct 28, 2018
Activities include a theme parade, ice cream social, parade of flags, games and crafts, and even bingo (aka samgo).

Sailwinds Park East Kite Festival - Cambridge, MD - Oct 28, 2018
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

Maryland Irish Festival - Timonium, MD - Nov 9 to Nov 11, 2018
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 16 to Nov 18, 2018
Explore artist and crafter booths at the Montgomery County Fairgrounds for a weekend of artistic appreciation and entertainment for all.

Maryland Ave Fall Festival – Annapolis, MD – October 21, 2018

Find other fun things to do in Maryland in the fall:

Oktoberfest in Maryland
Maryland Corn Mazes
Maryland Ghost Tours
Haunted Houses in Maryland
Pumpkin Patches in Maryland

3 thoughts on “Fall Maryland Festivals

  1. David Bailey says:

    This will be my first October fest, maybe when i was a kid I went but that was a long time ago. I will be volunteering in Wesminster, So I am really hoping this will be FUN.
    I think we all need to get out and have a lil bit of FUN now and again!! 😀

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