Fall Day Trips: Where to Go This Season Around Anne Arundel County
Fall around here doesn't creep in quietly. It shows up all at once, hayrides, corn mazes, apple cider donuts, and a full calendar of local farms and festivals that turn a Saturday into a real outing. Here's where to spend it this season, without leaving the county.
Homestead Gardens Fall Festival, Davidsonville
Every Saturday and Sunday from late September through late October, Homestead Gardens runs its Annual Fall Festival, one of the longest-running traditions in the county. A corn maze, pumpkin patch, barnyard animals, hayrides, a corn cannon, pony rides, and a full lineup of carnival games make this an easy full-afternoon trip, especially if you've got young kids in tow.
Y Worry Farm, Davidsonville
For a smaller, more low-key pumpkin patch experience, Y Worry Farm has been family-owned in Davidsonville for over three decades. A 5-acre patch, a small corn maze, and a corn stalk teepee make it a great stop for younger kids who might find a bigger festival overwhelming.
Knightongale Farm, Harwood
Just south in Harwood, Knightongale Farm has become a genuine local tradition for pumpkin picking, corn mazes, and hayrides. Free activities like the straw bale playground and petting farm round it out as one of the better values in the area for a family outing.
Kinder Farm Park Fall Fun Day, Millersville
Kinder Farm Park hosts its Fall Fun Day each October, built specifically for kids 12 and under. A straw-bale maze, scarecrow hayride, farm animal encounters, and a farmhouse tour make this one of the more hands-on fall events in the county. Registration and prepayment are required, so plan ahead rather than showing up on a whim.
Hancock's Resolution Harvest Festival, Pasadena
For something with a little more local history behind it, Historic Hancock's Resolution in Pasadena hosts its Harvest Festival each October, with seasonal crafts and demonstrations that lean into the cultural and communal side of the season rather than just rides and games.
Willow Oak Flower & Herb Farm, Severn
Willow Oak Flower & Herb Farm runs its Fall Harvest Day each October, with pumpkin picking, pumpkin painting, and more involved activities like building a dried flower pumpkin or a fairy garden. It's a good option for families who want fall activities with a slightly more creative bent.
Waugh Chapel Towne Centre Family Fall Festival
Right in the Crofton and Gambrills shopping hub, Waugh Chapel Towne Centre hosts its own Family Fall Festival, with balloon art, live music, pumpkin decorating, and kids' activities, an easy add-on if you're already running errands in the area.
Annapolis Fall Harvest Festival and Haunted Harbour Day
Annapolis Recreation and Parks hosts a free Fall Harvest Festival at the Pip Moyer Recreation Center each October, complete with a magic show, hayrides, a pumpkin patch, and trunk-or-treating. Downtown, Haunted Harbour Day along Maryland Avenue brings costume contests, trick-or-treating, and giveaways for a spookier, more walkable version of the same fall spirit.
Twist and Stout Festival, Quiet Waters Park
For the adults who'd rather sip than trick-or-treat, Twist and Stout at Quiet Waters Park in Annapolis is a wine and craft beer festival set against one of the prettiest parks in the county, a great way to spend a crisp fall afternoon without a single hayride in sight.
Don't Forget the Maryland Renaissance Festival
If you haven't already made it out to Revel Grove in Crownsville, fall is exactly when the Maryland Renaissance Festival is in full swing, running weekends through late October. It deserves its own trip if you haven't been.
Why This Season Matters Beyond the Fun
Every year, I watch families discover a neighborhood for the first time because they showed up for a pumpkin patch or a harvest festival and realized how much they liked the area around it. Fall has a way of showing off a community better than almost any other season, the farms, the festivals, the sense of neighbors gathering in one place. If you're weighing a move, a fall weekend spent exploring is one of the best ways to get a real feel for where you might actually want to live.
If you fall in love with a neighborhood this season, literally or otherwise, I'd love to help you explore what's available there.
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Bonnie Fleishman has specialized in waterfront and move-up real estate across Anne Arundel County for 36 years, serving Pasadena, Glen Burnie, Severna Park, Arnold, Crofton, Gambrills, and Annapolis. Festival dates and hours can shift year to year; confirm current details directly with each farm or venue before you go.
