Best Fall Activities in the DMV

Oct 8, 2018 | Fun Things To Do With Kids in MD, DC, and VA

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Find Family Fun at Pirate Adventures

Set sail in search of fun with us and experience a Pirate Adventure with your family aboard the pirate ship Sea Gypsy in the Annapolis Harbor.

Find the Best Fall Activities for Kids in the DMV

There are SO many fall activities for kids in the DMV that sometimes it can be hard to decide what to do first.  Plan your best fall ever with our giant list of kid’s activities near you.

Special Events At Pirate Adventures

Petes Pumpkin Patch Fall Activities for Kids


Fall makes a perfect time to visit us at Pirate Adventures in Annapolis.  Get your family out on the water and soak up the fall sunshine on the Chesapeake Bay.  We offer lots of special events in the fall including our famous Pirate and Princess cruise with Ariel, Moanna, and Tinkerbell.  Join us in October for Pirate Pete’s Pumpkin Patch and take home a pumpkin and get a chance to decorate it after your cruise.

Stay and play by the water in our gorgeous hometown of Annapolis after your Pirate Adventure.  There are plenty of fun things to do with kids while visiting Annapolis, find out our top picks here.  The historic city of Annapolis makes a great day trip from Washington DC and Baltimore in the fall.  Plan your trip around a special event in Annapolis, and find fall fun for the whole family.

The Best Pumpkin Patches in Maryland, DC, and Virginia

Pumpkin Patch Play near Annapolis

What would fall be without a pumpkin patch?  Pumpkin patches abound in the DMV from over the top fall attractions to family-run farm stands.  Our top picks are listed below.

Butlers Orchard

Find plenty of pumpkins and lots of other uniquely fall activities for kids at Butlers Orchard in Germantown, Maryland.  Butlers Orchard operates Tuesday through Sunday from September 29th through October 28th, 2018.

Montpelier Farms

With a huge pumpkin patch, Montpelier Farms makes a great place to start your quest for the perfect pumpkin.  Pumpkin bowling,  scarecrow building as well as a pumpkin patch and more fall activities for kids can be found on the farm.  Montpelier Farms is located in Upper Marlboro Maryland,  The pumpkin patch operates from September 15th through November 4th on Saturdays and Sundays and Friday afternoons.

Pirate Pete’s Pumpkin Patch

If you are looking to get beyond the farm join us on a Pirate Adventure with your kids and return to shore to pick out your perfect pumpkin.  Search for sunken treasure, fire the water cannons and celebrate Halloween with us.  Pirate Pete’s Pumpkin Patch is a unique place to get your pumpkin in Annapolis.  Free pumpkins are included with every child admission as well as a decorating station on site.  Don’t miss our pirate clubhouse transformed for the Halloween season.

Rock Hill Orchard

If pick-your-own is what you’re after Rock Hill Orchard offers pumpkins in addition to apples.  Don’t miss the homemade ice creamery on site for a special treat.  Rock Hill Orchard is located in Mount Airy Maryland and is open through the first weekend in November.

Sharps at Waterford Farm

Goats, chickens, a corn maze, pumpkin patch including a hayride make for a complete fall day at the farm.  Sharp’s Farm is located in Brookeville, Maryland and their pumpkin patch is open Saturdays and Sundays from September 29th through November 4th.

Looking for more pumpkin patches?  Check out our post about pumpkin patches near Annapolis, all within reach of Pirate Adventures.  If you want to continue the pirate theme this Halloween, check out our pirate themed pumpkin carving ideas.

Fall Festivals Fit for Kids

Fall weather brings on festival season in the DMV.  Jousting tournaments, apple cider tastings, trick or treating, and more

Renaissance Festival

Located in Crownsville, Maryland just outside of Annapolis this festival signals fall for many families.  Get your hair braided, eat a turkey leg and talk to a knight.  The Maryland Renaissance Festival runs weekends from August 25 through October 21st.

US Power Boat and Sailboat Shows

At first glance, this might not seem like a kid-friendly event.  Trust us, it is loads of fun for kids to climb on and off all different kinds of boats.  The boats are there to be shown and the brokers are happy to accommodate kids.  The best part about the Annapolis Boat shows is that all of the boats are in the water and you get to enjoy a day on the water with your kids.  Wave to the pirate ship as we pass by and give us an Ahoy!

Boo Zoo Events

Fall makes a great time to visit the zoo. Due to less heat and humidity, the animals are more active in the fall.   Not to mention, there are plenty of fall activities for kids to choose from at the zoo.  Try ZooBoo at the Maryland Zoo, Boo at the Zoo at the National Zoo, or Pumpkin Village at Leesburg Animal Park.

Trail of Jack-O-Lanterns

Green Meadows Petting Farm Trail of Jack-O-Lanterns is the perfect not so scary event to get your little ones pumped for Halloween.  Located in Ijamsville, Maryland the Trail of Jack-O-Lanterns on Friday, Saturday, and Sunday evenings from mid to late October/

Harry Potter Festival

Are you a Harry Potter fan?  Get the chance to play Quidditch, get measured for a wand, or even mix magic potions at the Harry Potter Festival in Chestertown, Maryland.  The 5th annual Harry Potter Festival takes place on October 5th and 6th in 2018.  Find a schedule of events here.

Pumpkin Patches with Fall Festivals

Lots of places offer a pumpkin patch along with a fall festival offering other fall activities for kids.  Fall festivals include corn mazes, hill slides, and even pumpkin cannons. Try Homestead Gardens, Green Street Gardens or Ticonderoga Farms.

Off the Beaten Path Fall Activities with Kids

Find fall family fun that remains somewhat undiscovered around the DMV.  Fall hikes as well as bike rides, not to mention unique playgrounds.

Scout the perfect playground

Go on a hunt for a new favorite playground this fall.  Find plenty of options with our big list of playgrounds in the DMV.  If your kids are into pirates or you want to get them pumped for a Pirate Adventure with us visit a pirate playground near you.

Hit the Trail

Getting outdoors before the weather makes us retreat to indoor activities with kids is what fall is all about.  Hike to the beach at Calvert Cliffs or Flag Ponds Nature ParkHike to a hidden waterfall, or scramble the rocks at the Billygoat trail at Great Falls or Bearfence Trail in Shenandoah.

Two Wheeling Treks for Kids

Who doesn’t love a bike ride together with some fall foliage?  For a flat, paved route perfect for kids try the Baltimore and Annapolis rail trail or the Cross Island Trail on Kent Island.

Discover Someplace New

If you are looking for fall adventures with the kids sometimes it’s best to just pick someplace new.  Come to see us at Pirate Adventures for an adventure on the water like no other!  For additional fall activity inspiration check out our lists of more amazing places to visit with kids in the DMV.  Try 101 Things to Do with Kids in Maryland or our A to Z Guide for Kids Activities in the DMV.  Fall is waiting, more importantly, winter will be here before you know it, get out there and explore!