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Fall Fun Awaits: Fall Festivals in Maryland

September 25, 2025 by Ricky Hartford

When the air turns crisp and the leaves start to glow with color, it can only mean one thing: fall festival season. Maryland know how to celebrate autumn in style, with hayrides, pumpkin patches, live music, and more activities than you can fit into a single day.

Here are some of our favorite fall festivals.

Annapolis Fall Harvest Festival (Annapolis, MD)

Mark your calendars for Saturday, October 25 from 10 a.m. to 2 p.m. — Annapolis Recreation and Parks is hosting a free Fall Harvest Festival at the “Pip” Moyer Recreation Center. This family-friendly event has something for everyone: a spooky magic show, hay rides, a pumpkin patch, face painting, and plenty of candy at Trunk-o’-Treating. Kids can even join a Superhero Training Camp with Batman, Black Panther, and Spider-Man or sing along with Elsa, Mirabel, and Tiana at the Princess Sing-Along. With costumes, community fun, and photo ops galore, it’s a spooktacular way to celebrate fall close to home.

Butler’s Orchard Pumpkin Festival (Germantown, MD)

If you want the ultimate fall day trip, Butler’s Orchard has it all. There’s apple picking, hayrides, corn mazes, barnyard animals, giant slides, live music, and even a pumpkin cannon for the thrill seekers. When everyone’s ready for a break, head to The Farmer’s Porch for sandwiches, pizzas, and seasonal bites made with farm fresh ingredients. Butler’s crams one trip into a full day of memories.

Councell Farms Field of Fun (Easton, MD)

On Maryland’s Eastern Shore, Councell Farms has turned fall into pure family fun with their beloved Field of Fun. For just $6 admission (kids under 2 are free, and grandparents tag along at no charge), families can enjoy more than 20 activities, including a corn maze, jumping pillow, and the popular John Deere combine slide. Open through October, it’s an easy tradition to fit into your family’s fall calendar.

Beyond the fun, you’ll find local apples, fresh cider, jams, jellies, and all the fall décor staples like gourds, mums, and straw bales. Don’t skip The Creamery, where Councell serves Vanderwende’s rich, creamy ice cream in rotating flavors, the perfect way to top off a day at the farm.

Gaver Farm Fall Fun Fest (Mt. Airy, MD)

With more than 65 attractions, Gaver Farm’s Fall Fun Fest is one of the biggest autumn celebrations in Maryland. Open daily through November 2, the festival features everything from giant slides and pedal karts to a 7-acre corn maze, a low ropes course, playgrounds, and jumping pillows. On weekends, you’ll also find extras like ziplining, cow train rides, and gem mining. Bonus — hayrides are always free, whether you’re taking in the farm views or heading to pick pumpkins, apples, or sunflowers.

Homestead Gardens Fall Festival (Davidsonville, MD)

Homestead Gardens turns into a fall wonderland on weekends through October 26. Families can enjoy pony rides, tractor hayrides, inflatables, a straw maze, and live music in the barnyard. Kids will love the jump pad, pumpkin and pollinator trains, and barnyard animals, while parents can relax under the shade tents or shop seasonal décor and baked goods.

Food is a highlight here too, with BBQ, food trucks, Lola’s Ice Cream, and those locally famous apple cider donuts. Adults can stop by The Beer Farm or enjoy wine and spirits tastings from local producers like The Vineyards at Dodon and Grey Wolf Distillery. Pro tip: wristbands are required for most kid activities, but plenty of food, drinks, and shopping are open to all, making this festival a great mix of family fun and community spirit.

Knightongale Farm Fall Festival (Harwood, MD)

Right here in Anne Arundel County, Knightongale Farm’s Fall Festival has become a favorite fall tradition for families. Open through October 26, the farm offers pumpkin picking, a corn maze, hayrides, pedal tractors, barnyard basketball, and a giant jump pad. What makes Knightongale stand out is its local flair. This 82-acre working farm is family-owned, with plenty of food, drinks, and even on-site beer and wine from nearby producers. 

Larriland Farm (Woodbine, MD)

Larriland’s fall celebrations feel like the season in full color. Kids can wander through the Boo Barn, explore the straw maze, and climb aboard hayrides that roll through Halloween-decorated woods. The whole family will love the farm’s festive atmosphere, complete with food trucks and warm apple fritters on the weekends. It’s a perfect mix of cozy and just a little spooky.

Magnolia Meadow Farms Fall Festival (Thurmont, MD)

Magnolia Meadow Farms has quickly become a viral favorite and with a massive corn maze, apple cannons, zip lines, mountain slides, and pumpkin bowling, it’s easy to see why. Open from through November 2, weekends here are packed with activities like barrel trains, pedal karts, jumping pillows, hayrides, and farm animal encounters. The fun doesn’t stop when the sun goes down: Moonlit Maze nights on October 11 and 25 keep the farm open late, complete with live music and glow sticks under the stars.

The food scene is just as much of a draw as the activities. From soft pretzel flights and brisket nachos to pumpkin soft serve, apple cider donuts, and even cider floats, there’s something to satisfy every craving. Adults can grab a local craft beer, cider, or wine flight, while kids sip strawberry lemonade or hot chocolate.

Maryland Avenue Fall Festival (Annapolis, MD)

Set in the heart of Annapolis, the Maryland Avenue Fall Festival is a small-town celebration with big personality. On Sunday, October 19, from 10 a.m. to 5 p.m., the first two blocks of Maryland Avenue transform into a street fair filled with antiques, handmade goods, local vendors, and plenty of fall treats. Stroll with a cup of cider in hand, listen to soft jazz spilling from front porches, and enjoy the community atmosphere that has made this one of the state’s longest-running festivals.

Families will love the kid-friendly activities and the Halloween Pup Parade, while shoppers can browse everything from vintage finds to artisan crafts. With food trucks, live music, and that unmistakable Annapolis charm, this festival is the perfect way to spend a fall day close to home.

Maryland Renaissance Festival (Crownsville, MD)

No list of Maryland fall traditions would be complete without a nod to the Maryland Renaissance Festival. Tickets for 2025 are already sold out, but a limited number of refunded tickets are released online each Monday, so it’s worth checking back if you’re hoping to snag one. If you’ve already secured your spot in Revel Grove, don’t miss our full guide to the festival for tips on everything from jousts and shows to feasting and kid-friendly fun. Huzzah!

Milburn Orchards BIG BackYard Fall Festival (Elkton, MD)

Milburn Orchards takes “festival” to the next level. The BIG BackYard is loaded with activities like the Bale Trail straw maze, the Milburn 500 pedal cart racetrack, King Kong ping pong, and even a paintball shooting gallery. Add in hayrides, pony rides, farm animals, and giant play areas, and you’ve got an all-day adventure. Don’t forget to stop by their market for cider, pies, and other fall goodies to take home.

Montpelier Farms Fall Festival (Upper Marlboro, MD)

Montpelier Farms is one of the region’s most popular fall spots, and their annual festival proves why. The farm is buzzing with activities like pig races, pumpkin bowling, barnyard basketball, puzzle mazes, and a giant 7-acre “Once Upon a Time” themed corn maze. Younger kids can enjoy the Spookley the Square Pumpkin maze, while others can race down giant hill slides or try their luck at the roping range.

The fun doesn’t stop with the activities. Guests can refuel with brick oven pizza, BBQ sandwiches, apple fritters, or hot cider donuts, and adults can even grab a beer or mead wine from Crooked Crab Brewing. Pro tip: tickets can sell out on peak weekends, so grab them online in advance to make sure you don’t miss out on the farm fun.

Summers Farm Fall Festival (Middletown, MD)

Summers Farm has been a fall favorite for nearly 30 years, and it’s easy to see why. Through October 31, the farm is a playground with more than 45 attractions, including giant slides, pumpkin train rides, a five-acre corn maze, zip lines, rubber ducky races, and barnyard animals. Kids can bounce on jumping pillows, dig into corn pits, or roll over round bales, while grown-ups can test their aim at the Apple Blasters or kick back with farm-fresh food. Wagon rides, pumpkin picking, and endless photo ops make it the kind of place you’ll want to return to year after year. Pro tip: check their calendar before you go, since the farm is closed on select weekdays during the season.

Weber’s Fall Harvest Days (Parkville, MD)

Weber’s knows how to do fall right. Their Harvest Days are packed with fun for all ages, from duck races and hillside slides to tire climbs and hayrides. Families can enjoy a spooky walk that’s kid-friendly, check out farm animals, or pan for gems at the trading post. Live music, food trucks, and fall treats like cider donuts and apple slushes make this festival as delicious as it is entertaining.

Check out a few additional fall festivals you may not want to miss:

  • AACS Fall Festival (September 27)
  • Fall Festival on the Green (September 27)
  • Oktoberfest (September 28)
  • Barktoberfest (October 4)
  • GBIA FallFest (October 4)
  • Harvest Bash (October 11)

Each festival brings its own spin on fall fun, whether it’s a corn maze, live music, or a sweet treat you can only get once a year. Schedules and activities can change quickly as the season goes on, so it’s worth checking their websites or socials before you head out. However you celebrate, these festivals are all about soaking up the season, making memories, and maybe finding a new family tradition along the way.

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Category: CommunityTag: Activities, Fall, fall festivals, Family Friendly See all posts by Ricky Hartford

About Ricky Hartford

Ricky Hartford is fueled by cold brew, Celtics highlights, pop culture, and a perfectly placed Oxford comma. By day, he works in marketing and communications at Anne Arundel Community College, where he helps shape the college’s voice through content and storytelling. With over a decade of experience and a Master of Science in Strategic Communications, he’s helped nonprofits and local publications sound sharper, look better, and connect more clearly with their audiences. When he’s not working, he’s probably at the movies, on the basketball court, planning his next vacation, or convincing someone (anyone) to talk about the latest trashy reality show. Annapolis is his happy place, especially if it involves a drink downtown and hanging out by the water.

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