Fall Fun in Anne Arundel County: What to Do This Week & Weekend, October 8–11, 2026
October has a way of making Anne Arundel County feel a little extra special. Temperatures start to cool, pumpkins appear on porches and farm stands, and weekends suddenly feel made for getting outside, wandering around Annapolis, or piling everyone into the car for an afternoon of fall fun.
This week and weekend, October 8–11, there is plenty happening around Anne Arundel County. Whether your perfect October outing involves boats along the Annapolis waterfront, enormous pumpkins, a hayride through a local farm, a little history with a spooky twist, or an evening around a campfire, you'll find wonderful ways to enjoy fall close to home.
Head to the Annapolis Waterfront for the Powerboat Show
Few events say “Annapolis” quite like a boat show, and the Annapolis Powerboat Show returns October 8–11 in historic downtown Annapolis. City Dock and the surrounding harbor will once again become a gathering place for boaters, waterfront lovers and visitors who simply enjoy being part of one of the city's signature traditions.
You certainly don't have to be shopping for a boat to enjoy the atmosphere. There are boats to explore, marine exhibitors to browse and plenty happening around downtown, making this an easy excuse to spend a fall day near the water and then wander into town for lunch, shopping or an early dinner.
One important local tip: give yourself some extra time. The City of Annapolis is warning visitors about road closures, detours and parking restrictions associated with the fall boat shows, particularly around downtown and the Historic District.
Meet the Great Annapolis Pumpkins
There are pumpkins, and then there are Annapolis pumpkins.
The Great Annapolis Pumpkins return downtown this weekend, with the giant gourds going on display beginning October 10. These aren't oversized decorations made to look real. They are actual pumpkins selected from regional giant-pumpkin competitions, with many weighing more than 1,000 pounds.
They have become one of those wonderfully quirky Annapolis fall traditions that practically demand a photo. Make a morning or afternoon of it by finding the pumpkins, walking the historic streets, stopping into local shops and enjoying everything downtown has to offer during an October weekend.
Visit Annapolis is also welcoming fall with Fall Fest on Saturday, October 10, so this is an especially good weekend to head downtown and soak up the season.
Spend a Classic Fall Day at Homestead Gardens
For families who want pumpkins, hayrides, and all the traditional fall favorites in one place, Homestead Gardens in Davidsonville is hosting its Fall Family Weekends Saturday and Sunday, October 10 and 11, from 10 a.m. to 4 p.m.
This outing feels like childhood fall weekends all over again. Families can enjoy tractor hayrides, barnyard animals, a hay maze, pumpkin painting, a pumpkin patch, pony rides, live music, seasonal foods, sweet treats and plenty of activities for younger visitors. Fall plants and décor to browse also make it hard to leave without at least one mum or pumpkin coming home with you.
Enjoy an Old-Fashioned Farm Day in Harwood
If your idea of fall involves open fields, pumpkins and a real working farm, Knightongale Farm Pumpkin Patch & Fall Festival in Harwood is another local favorite worth considering this weekend.
The 82-acre working farm is known for its weekend fall festival and pumpkin patch, with uncomplicated outdoor activities that make a beautiful October day feel like October should. It's an especially nice option for families looking to get away from the busier Annapolis waterfront and spend a few hours enjoying southern Anne Arundel County.
Wear shoes that can handle a farm field, especially if it's been raining, and embrace the possibility of a little dirt. That's part of the fun.
Try a Free Fall Saturday at Ridge Grow
Not every family outing needs to turn into an expensive day, which makes Free Fall Saturdays at Ridge Grow in Annapolis especially appealing. On Saturday, October 10, from 10 a.m. to 5 p.m., visitors can enjoy pumpkins, mums, food trucks, yard games and seasonal family activities.
There's a playground, putt-putt, pumpkin bowling and a pumpkin patch, giving families plenty to do without having to travel far from Annapolis. It's also a good choice when you don't necessarily want to commit an entire day to one event but still want to get outside and enjoy a little fall atmosphere.
Pumpkins, Crafts and a Little Local History at Kinder Farm Park
Sunday brings another great family option at Kinder Farm Park in Millersville. Pumpkins and Crafts takes place October 11 from 11 a.m. to 2 p.m., followed by the park's Blacksmith Shop Workday from 1 to 4 p.m.
Kinder Farm Park is already one of those places where it's easy to spend more time than you intended. With its agricultural setting, trails, farm history and wide-open spaces, it fits especially well into a crisp October Sunday.
The blacksmith demonstration adds something a little different, too. Instead of another purely seasonal attraction, families get a glimpse into the county's agricultural past while enjoying one of Anne Arundel County's best-known regional parks.
Add a Little Spooky Annapolis History
October and historic Annapolis are a pretty natural combination. Once evening arrives and the old streets get a little quieter, centuries of local history provide the perfect setting for ghost stories, legends and a few tales that might make you look over your shoulder.
Historic ghost tours run on select October dates, along with the Annapolis Witches & Legends Walking Tour, which explores Maryland witch trials, colonial superstitions, and local legends. Beginning October 9, the Very Superstitious! Paca House & Garden Tour also explores the beliefs, rituals and lucky charms that were part of everyday life centuries ago.
It's a fun alternative for adults, couples or families with older kids who have graduated from pumpkin patches but still want to do something distinctly October.
End the Weekend Around a Campfire at Thomas Point
There may not be a more fitting way to close an Anne Arundel County fall weekend than beside a fire with the Chesapeake Bay nearby.
On Sunday, October 11, from 6 to 7:30 p.m., Anne Arundel County Recreation and Parks is hosting a Campfire Chat at Thomas Point Park in Annapolis.
Thomas Point Park sits where the South River and Chesapeake Bay come together, giving it a completely different feel from the farms and downtown activities on this list. October evenings along the water can also feel considerably cooler than they do inland, so bring an extra layer and settle in for a very Maryland way to finish the weekend.
This Is Why Fall in Anne Arundel County Is So Easy to Love
One of my favorite things about living in Anne Arundel County is that you don't have to travel very far to completely change the feel of your day. You can start among boats and brick-lined streets in downtown Annapolis, spend the afternoon picking pumpkins on a farm in Davidsonville or Harwood, wander through a historic park in Millersville, and finish the weekend beside the Chesapeake Bay.
Those experiences are part of what makes a community feel like home. Knowing the neighborhoods is important, but knowing the traditions, hidden corners, weekend favorites and little things residents look forward to every year is part of understanding Anne Arundel County, too.
If you're thinking about buying, selling or making a move anywhere in Anne Arundel County, Bonnie Fleishman brings that local perspective to the conversation. From waterfront communities and established neighborhoods to the quieter corners of the county, Bonnie understands that choosing a home isn't simply about bedrooms, bathrooms and square footage. It's about finding the community and lifestyle that feel right for you.
Enjoy the pumpkins, grab the sweater, get outside and make the most of this beautiful October weekend. Fall in Anne Arundel County doesn't last nearly long enough, so this is a very good weekend to enjoy it.
