Funtober Fall Festivals

Fall Maryland Festivals

This list of fall festivals in Maryland displays an excellent array of harvest, music, and food festivals to follow up on Maryland’s Oktoberfest celebrations.

We hope you enjoyed last year’s list.  We will be updating this information for 2016 over the next few weeks.  Stay tuned!

Last Major Update:


Fall Festival Organizer? Advertise Here.
More than 500,000 people came to Funtober last year looking to attend a fall festival and another 500,000 were specifically interested in attending an oktoberfest. We can help increase attendance at your event through a sponsored listing, coupon giveaway, cross-promotion or other creative marketing initiative. Special deals for nonprofits. Please see our advertising page or contact us for more information.

September 2016

Maryland State Fair – Lutherville-Timonium, MD – August 25 – September 5, 2016
An annual state fair held at 2200 York Road.  Enjoy carnival rides, thoroughbred horseracing, livestock shows, kiddie rides, and great carnival style food.

Vegan SoulFest – Baltimore, MD – August 20, 2016
Lots of exhibitors, guest speakers, live entertainment, cooking demonstrations, and more about the vegan lifestyle. Held annually at the Baltimore City Community College at 2901 Liberty Heights Avenue.

National Hard Crab Derby – Crisfield, MD – September 2-4, 2016
Features live entertainment, music, parade, fireworks, carnival rides, beauty pageant, races, contests and lots of family fun with crafts, arts, and more vendors.

Baltimore Comic Con – September 2-4, 2016
Considered “America’s Greatest Comic Book Convention” is held annually Labor Day weekend at the Baltimore Convention Center.

Deep Creek Lake Art & Wine Festival – Deep Creek, MD – September 9-11, 2016

In the Street Festival – Frederick, MD – September 10, 2016
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 – September 10-11, 2016
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 – September 10-11, 2016
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.

High Zero – September 15-18, 2016
A music festival of live experimental improvised music with lots of performers.

DogFest – Baltimore, MD – September 17, 2016
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.

Annapolis Craft Beer and Music Festival – Annapolis, MD – September 17, 2016
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 Wine Festival – Westminster, MD – September 17-18, 2016
Features wine samplings, guided tours of the Museum’s Farmhouse, and continuous live entertainment.

Westminster Fall Fest – Westminster, MD – September 22-25, 2016
An annual event held in Westminster.  Features a parade, fun run, craft vendors, food court and fun.

Sunfest – Ocean City, MD – September 22-25, 2016
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.

Baltimore Book Festival – Sept 23-25, 2016
A full weekend of books, demonstrations, readings, stage shows and more.

Island Bay Day – Grasonville, MD – September 24, 2016

Maryland Microbrewery Festival – Westminster, MD – September 24, 2016
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.

October 2016

Taste of Bethesda – Bethesda, MD – October 1, 2016
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.

Takoma Park Street Festival – Takoma, MD – October 2, 2016
Enjoy the 35th annual festival held on Carroll Avenue.  Features local artists, and crafters who offer paintings, pottery, silk-screening, stained glass, woodworking, textiles and ceramics along with plenty of food trucks.

Fell’s Point Fun Festival – Sept 30 – Oct 2, 2016
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.

La Plata Fall Festival – La Plata, MD – October 6, 2016

Baltimore Beer Week – Baltimore, MD – October 7-16, 2016
Celebrate the 8th year of this annual event.  Kinda runs with the Das Best Oktoberfest held next door.

Good Beer Festival – Salisbury, MD – October 8-9, 2016
Over 100 different craft beers and unlimited tastings from master brewers.  Features include an electric music line-up, and the Sports Zone with telecast of the biggest games.  Held at the Pemberton Historical Park.

Maryland Pumpkin Festival – Frederick, MD – October 8-9, 2016
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, egg hunt, candy shoot, and some painting and sculpturing demonstrations.

Autumn Glory Festival – Garrett, MD – October 12-16, 2016
An annual event with two large parades, live music concerts, band competitions, art exhibits, craft shows and of course plenty of foods.  Celebrate the beauty of fall foliage.

Baltimore Running Festival – Baltimore, MD – Oct 15, 2016
Over 5 distance options for runners of all abilities.

U.S. Oyster Festival, Maryland – California, MD – October 15-16, 2016
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.

Hereford Fall Festival – Hereford, MD – October 15-16, 2016
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.

Maryland Wine Festival – Salisbury, Maryland – October 15-16, 2016

Sailwinds Park East Kite Festival – Cambridge, MD – October 23, 2016

Chesapeake Film Festival – Easton, MD – Oct 27-30, 2016

November 2016

Maryland Irish Festival – Timonium, MD – Nov 11-13, 2016
A cultural event with workshops, demonstrations, traditional food, Irish Dancers, live music, food, beer, and arts and crafts.

Future Events – 2017

If we find the dates for a festival next fall (September or October 2017) which does not have an event in 2016, we will post them here.

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!

Maryland Ave Fall Festival – Annapolis, MD – September 20, 2015

The Shindig – Not happening in 2016.

Find other fun things to do in Maryland in October:

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


  1. 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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