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.

Last Major Update:


Aberdeen Fall FestivalsBaltimore Fall FestivalsEastern Shore Fall FestivalsFrederick Fall Festivals

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Vegan SoulFest - Baltimore, MD - Aug 20 to Aug 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.

Maryland State Fair - Lutherville-Timonium, MD - Aug 25 to Sep 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.

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

National Hard Crab Derby - Crisfield, MD - Sep 2 to Sep 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.

Deep Creek Lake Art & Wine Festival - McHenry, MD - Sep 9 to Sep 11, 2016

In the Street Festival - Frederick, MD - Sep 10 to Sep 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 - Sep 10 to Sep 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 - Sep 10 to Sep 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 - Baltimore, MD - Sep 15 to Sep 18, 2016
A music festival of live experimental improvised music with lots of performers.

Annapolis Craft Beer and Music Festival - Annapolis, MD - Sep 17 to Sep 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.

DogFest - Baltimore, MD - Sep 17 to Sep 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.

Maryland Wine Festival - Salisbury, MD - Sep 17 to Sep 18, 2016
Features wine samplings, guided tours of the Museum’s Farmhouse, and continuous live entertainment.

Sunfest - Ocean City, MD - Sep 22 to Sep 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.

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

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

Island Bay Day - Grasonville, MD - Sep 24 to Sep 24, 2016

Maryland Microbrewery Festival - Westminster, MD - Sep 24 to Sep 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.

Fell’s Point Fun Festival - Baltimore, MD - Sep 30 to 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.

Taste of Bethesda - Bethesda, MD - Oct 1 to Oct 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 - Oct 2 to Oct 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.

La Plata Fall Festival - La Plata, MD - Oct 6 to Oct 6, 2016

Good Beer Festival - Salisbury, MD - Oct 6 to Oct 10, 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.

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

Maryland Pumpkin Festival - Frederick, MD - Oct 8 to Oct 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 - Oakland, MD - Oct 12 to Oct 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 to Oct 15, 2016
Over 5 distance options for runners of all abilities.

Hereford Fall Festival - Hereford, MD - Oct 15 to Oct 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 - Westminster, MD - Oct 15 to Oct 16, 2016

U.S. Oyster Festival, Maryland - California, MD - Oct 15 to Oct 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.

Sailwinds Park East Kite Festival - Cambridge, MD - Oct 23 to Oct 23, 2016

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

Maryland Irish Festival - Timonium, MD - Nov 11 to Nov 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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