Fall weekends in Annapolis and Anne Arundel County offer far more than pumpkin shopping.
You can walk through an eight-acre corn maze, take a hayride across a working farm, visit barnyard animals, pick pumpkins directly from the field, or find a 1,000-pound pumpkin sitting in the middle of Downtown Annapolis.
These are seven of our favorite places to enjoy fall across the communities the Brad Kappel Team serves.
GREAT ANNAPOLIS PUMPKINS
Downtown Annapolis
BEST FOR: A DISTINCTLY ANNAPOLIS FALL TRADITION
The Great Annapolis Pumpkins prove you do not need to leave downtown to enjoy pumpkin season.
The massive pumpkins return to locations throughout Annapolis on October 10. They remain on display through October before local artists transform them into oversized jack-o’-lanterns on October 29. The pumpkins are scheduled for removal by November 2.
Make an afternoon of it. Find the pumpkins, walk the brick streets, stop for lunch, and enjoy fall along City Dock.
This is the best option for anyone who wants seasonal photos and an Annapolis experience without committing to a full farm day.
PLAN YOUR VISIT: Visit Annapolis Great Annapolis Pumpkins
HOMESTEAD GARDENS
Davidsonville
BEST FOR: A COMPLETE FAMILY FALL DAY
Homestead Gardens is known for its plants, home décor, and seasonal displays, but its Fall Family Weekends turn the Davidsonville property into a full fall destination.
Families can enjoy tractor hayrides, pony rides, barnyard animals, hay mazes, pumpkin activities, bounce attractions, live music, seasonal food, and apple cider doughnuts. The pumpkin patch and fall market make it easy to bring part of the experience home.
The event is designed especially for families with children age 12 and younger.
Fall Family Weekends run Saturdays and Sundays through November 1 from 10 a.m. to 4 p.m.
PLAN YOUR VISIT: Homestead Gardens Fall Family Weekends
KNIGHTONGALE FARM
Harwood
BEST FOR: A CLASSIC LOCAL FARM EXPERIENCE
Knightongale Farm has been a fall tradition in southern Anne Arundel County for 25 years.
The working farm offers a pumpkin patch, corn maze, hayrides, petting animals, pedal tractors, a jumping pad, a large slide, and barnyard basketball. Food, drinks, pony rides, face painting, and additional activities are also available.
Knightongale feels local because it is local. The 82-acre family-owned farm sits along Route 2 in Harwood and has welcomed generations of Anne Arundel County families.
Fall Fest runs weekends through October 25 from 10 a.m. to 5 p.m.
PLAN YOUR VISIT: Knightongale Farm
GREENSTREET GARDENS
Lothian
BEST FOR: A BIG CORN MAZE AND A FULL DAY OUTSIDE
Greenstreet Gardens continues to expand its fall experiences. This year's centerpiece is a five-acre corn maze celebrating America’s 250th anniversary.
Admission includes the corn maze, hayrides, face painting, a jumping pillow, an underground slide, a tire playground, a corn pit, woodland access, and other family activities. Visitors can also feed the farm animals and shop for pumpkins, mums, and fall plants.
Greenstreet is a strong choice when your group wants enough activities to fill most of the day.
Bonus! Fall Festival weekends continue through November 8.
PLAN YOUR VISIT: Greenstreet Gardens Fall Festival
MD CORN MAZE
Gambrills
BEST FOR: THE BIGGEST ADVENTURE
The eight-acre MD Corn Maze is the most ambitious maze on this list. The 2026 design celebrates classic childhood toys, with a Toy Story-inspired experience and character appearances on select dates.
A worker stationed on a tower inside the maze can help guide visitors who lose their bearings.
Beyond the maze, the farm offers more than 30 activities, including hayrides, farm animals, slides, ziplines, slingshots, corn pits, and games. Select Saturday dates also offer the chance to experience the maze after dark.
MD Corn Maze is open on select weekdays and weekends through November 8.
PLAN YOUR VISIT: MD Corn Maze
Y WORRY FARM
Davidsonville
BEST FOR: SIMPLE, AFFORDABLE PUMPKIN PICKING
Y Worry Farm keeps pumpkin picking simple.
Admission is free. You pay for the pumpkins, gourds, squash, cornstalks, or other fall items you take home.
Visitors can walk the fields with a wagon, see chickens and goats, climb the straw pyramid, explore a cornstalk teepee, and make their way through a small corn maze.
The farm restocks its fields later in the season, making it a reliable choice for families who do not choose their pumpkins during the first weekend of October.
The pumpkin patch is open weekends in October from 10 a.m. to 6 p.m.
PLAN YOUR VISIT: Y Worry Farm
HANSEL HILL FARM
Millersville
BEST FOR: A FALL EVENING WITH A LITTLE SUSPENSE
Hansel Hill Farm offers two levels of Halloween fun.
The Not-So-Spooky Hayride gives younger children a friendly evening on the farm. The Sorta Spooky Orchard Walk adds a little more suspense for older children and adults without professional actors, chainsaws, or aggressive jump scares.
Hansel Hill is a small, veteran- and woman-owned farm focused on sustainability, education, and community. Its scale creates a more personal experience than the larger fall festivals.
Fall evening events take place on select weekends in October.
PLAN YOUR VISIT: Hansel Hill Farm Special Events
CHOOSING THE RIGHT FALL EXPERIENCE - FAQs
Choose Great Annapolis Pumpkins for a downtown walk and photos.
Choose Homestead Gardens or Greenstreet Gardens for a full family day.
Choose Knightongale Farm for a classic working-farm experience.
Choose MD Corn Maze for the largest maze and the most activities.
Choose Y Worry Farm for relaxed pumpkin picking without an admission fee.
Choose Hansel Hill Farm for an October evening with mild Halloween suspense.
FALL ACROSS ANNAPOLIS AND ANNE ARUNDEL COUNTY
These farms and traditions are part of everyday life in the communities we serve.
From Downtown Annapolis and West Annapolis to Davidsonville, Harwood, Lothian, Gambrills, and Millersville, every area offers its own version of fall in Anne Arundel County.
If you are considering a move within Annapolis, Anne Arundel County, the Chesapeake Bay region, or Maryland’s Eastern Shore, the Brad Kappel Team can help you understand the neighborhoods, lifestyle, and real estate opportunities behind each community.
Brad Kappel Team | Sotheby’s International Realty
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