Updated July 25, 2023

Explore Dorchester County – the Heart of the Chesapeake – this summer and find plenty of family-friendly outdoor adventures, interesting hands-on experiences, and fun! Let the kids take the wheel of a traditional oystering boat, pick berries from the plant, glide on a stand-up paddleboard, and much more. Our 2023 Family Fun Guide is chock full of ideas and we’re updating it regularly, so be sure to check back throughout the summer. Dorchester County on Maryland’s Eastern Shore is easy to get to – about 85 miles from Baltimore and Washington, DC. A good place to start is at the Dorchester Visitor Center, open 8:30am-4:30pm daily at 2 Rose Hill Place in Cambridge, where you’ll find information about things to do, friendly staff to answer questions, restrooms, plus exhibits on life here. Pick up a Dorchester Fun Book while you’re there!


Skipjack Nathan of Dorchester

At the helm on the Skipjack Nathan of Dorchester.



  • Field Day at the Refuge! Blackwater National Wildlife Refuge in Cambridge hosts an adventurous day of outdoor exploration, arts and crafts, and Hoverball archery for young nature explorers and aspiring archers. July 29 anytime from 11am to 2pm. Free! For more information, call 410-228-2677.
  • Grab the helm, help with the sails, and see what river critters they bring up in the dredge on an authentic Chesapeake Bay oyster dredging vessel during a Skipjack Nathan of Dorchester cruise. Reserve ahead.
  • Climb the spiral steps and enjoy the view at the Choptank River Lighthouse. Open daily 9:30-5pm with free admission.
  • Watch bald eagles, herons, egrets, and more soar at Blackwater National Wildlife Refuge. The visitor center has lots of kid-friendly exhibits plus a butterfly garden.
  • Kayaking in Dorchester County, Maryland | Visit Dorchester

    Kayaking with Blackwater Adventures. Photo courtesy Maryland Tourism.

    Paddle or pedal your way through beautiful landscapes and waterscapes with Blackwater Adventures, which offers both guided tours and kayak, SUP, and bike rental for you to explore on your own. (They even offer delivery to local vacation rentals.)

  • Learn to stand-up paddleboard or try floating yoga with Over Board Paddle & Fitness.
  • Go fish! Learn to cast a line at the Kids’ Fishing Derby  9am-12pm on Aug. 5 – for ages 5-12 at Long Wharf Park in Cambridge. Pre-register by July 31. Or get the whole family signed up with a fishing charter.
  • Ride ’em cowboy at Windy Way Horses – with rides, painted pony events, and summer camps.
  • The Dorchester County Pool at 107 Virginia Ave. in Cambridge is open until August 20 for the 2023 season.


Handsell Historic Site in Dorchester County, Maryland

Handsell Historic Site includes a 1700s home and a Native American longhouse. Photo courtesy of Handsell.


Dorchester County is filled with interesting stories from the past – from Native American times to the county’s founding more than 350 years ago to maritime, Black history, and more.

  • Young history detectives can follow the footsteps of an American hero along the road trip known as the Harriet Tubman Underground Railroad Byway. The byway’s namesake Harriet Tubman was born here in Dorchester County 200 years ago. Don’t miss the new 12-foot “Beacon of Hope” sculpture and the moving “Take My Hand” mural. (Plus there’s a free Audio Guide!)
  • Travel back in time at Handsell Historic Site – step into the Native American longhouse, see the restored 1700s house, explore the lands and stories of three cultures. Summer Saturdays feature tours of the house and special programming, from foraging to flintknapping. (For the free Audio Tour, call 410-858-4173 on your cell phone)
  • Go on a treasure hunt with the Dorchester County Passport Tour; pick up what you need at the Dorchester Visitor Center, 2 Rose Hill Place in Cambridge.
  • Junior Ranger program at Harriet Tubman Underground Railroad Visitor Center

    Junior Ranger program at Harriet Tubman Underground Railroad Visitor Center.

    Earn a Junior Ranger badge (pictured here) at Harriet Tubman Underground Railroad State Park & Visitor Center. The center is also hosting daily programming on certain weeks in the summer, including Story Time with a Ranger at 10:30am July 28. They’ll also have short talks on various abolitionists July 25-30. See the schedule.

  • Call in the Ghost Busters on a Cambridge Ghost Walk along Maryland’s most haunted street (best for middle school on up).
  • Wander the grounds at Spocott Windmill & Village, which features a windmill and small village with a one-room schoolhouse, cottage and more that recreates a slice of life in the 1800s.
  • Experience the Dorchester County Historical Society with extensive artifacts and exhibits about farming, Native American life, the canning industry, decoy carving, historic buildings, and more.
  • Go big while exploring the self-guided Chesapeake Mural Trail – including a mural on a train caboose – and learn about local culture and people. (Free Audio Guide, too!)
  • Join a walking tour with live music performing Underground Railroad code songs with a banjo player, led by the Harriet Tubman Museum & Educational Center.


Cabin Fever Play Centre | Visit Dorchester

Arcade at Cabin Fever Play Centre.


Weather too rainy or hot for outside fun? Here are a few things to do indoors.

  • Cut loose at Cabin Fever Play Centre, with an extensive inside play structure, MEGA Brite, Ball Blaster, and plenty of arcade games to keep all ages happy.
  • Head to DoCo Axe Co. for axe-throwing (16 and over only) or have the family take on a virtual reality Escape Room (good for tweens and teens and older). Closed-toe shoes a must.
  • Wee Gamerz Videogame Bus Extravaganza brings multiplayer fun to the Cambridge branch of the Dorchester County Public Library Aug. 2 from 3 to 5pm. For ages 8-17. Questions? Call 410-228-7331.
  • Up your selfie game at POZE the Selfie Experience, a selfie museum, photo studio, and art space with lots of setups and props.
  • Sit back and watch movies at Cambridge Premier Cinemas.
  • Strike out on your own at Choptank Bowling & Billiards.
  • The Adrenaline Championship Wrestling Event is Aug. 20, 2-7pm hosted by Blue Ruin in Cambridge. Watch for updates here.
  • For Dorchester County residents, check out the many activities – from anime to crafts to STEM – going on at the Dorchester County Library, at both the Cambridge and Hurlock branches.


Playground at Sailwinds Park East, Cambridge, MD

Playground at Sailwinds Park East, Cambridge, MD


  • Hyatt Chesapeake Pool | Visit Dorchester

    Poolside fun at the Hyatt Regency Chesapeake Bay Resort. Photo courtesy of the Hyatt.

    Dive into family fun at Hyatt Regency Chesapeake Bay Resort with dive-in movies, indoor/outdoor pool with slide, mini-golf, disc golf, s’mores at the huge outdoor fireplace, game room, plus water sports (kayaks, SUPs, powerboats).

  • Swing over to a waterfront park or playground at Sailwinds Park East (right next to the Dorchester Visitor Center),  Gerry Boyle Park at Great Marsh, or Long Wharf Park, all in Cambridge.



Berry picking at Emily's Produce in Dorchester County, MD

Emily’s Produce offers pick-your-own berries and flowers.



  • Dig into a farm adventure and pick your own blackberries, blueberries, or wildflowers at Emily’s Produce. While you’re there, feed the goats, burn off some calories at Kyle’s Farm Fields of Fun, grab lunch or indulge in a scoop of Scottish Highland Creamery ice cream. On Wednesdays in July, Emily’s Produce invites ages 4 to 9 to join in some hands-on educational farm fun with their Farm Along With Emily’s.
  • Experience the fun of a county fair at the Caroline-Dorchester County Fair Aug. 2-5 with 4-H exhibit, barnyard exhibit, train display, animal shows, children’s day program, video game trailer, mechanical bull, and more. See the schedule.
  • Get a behind-the-scenes look during a morning chores farm tour of Pop’s Old Place on the first Sunday of the month. This century farm offers grass-fed beef and lamb as well as pastured pork, and more.
  • See billions of babies … oysters that is! at Horn Point Lab tours (Tuesdays at 10am) for ages 10 and up. Also check out Horn Point’s Kids Summer Adventures in August.
  • Stop by the waterfront Cambridge Farmers Market, each Thursday 3-6pm at Long Wharf Park in Cambridge.
  • Let the kids pick flowers as they like at Vintage Family Farms. Bring your own clippers. Open Thursday through Sunday.


Phippin's Crafting Corner - Cambridge, MD

Hands-on fun at Phippin’s Crafting Corner. Photo courtesy of Phippin’s.



  • DCHS - Whale craftGet your hands dirty with an ever-changing selection of craft projects at Phippin’s Crafting Corner, from bubble art to kids “paint and sip (juice)” sessions. They also have summer camps.
  • Mandala Pies hosts Little Whisks Culinary School for kids on Wednesdays in July, 10am-2pm, with time for free play and art in nature. They’ve also added new dates on Mondays: July 31, Aug. 7, Aug. 14. Join one session or all. Sign up at caitlin@mandalapies.com.
  • Sand and paint an adorable whale silhouette (pictured here) with a master carver at the Dorchester County Historical Society on Aug. 19 from 10am to 2pm. Best for ages 10-15. Only $5! Register at 410-228-7953 or dchs@verizon.net.
  • Check out the classes and workshops offered by the Dorchester Center for the Arts, including a (free!) four-week Teen Art Intensive.




Bay Country Bakery - Donuts - Dorchester County, MD

Donuts galore at Bay Country Bakery in Cambridge.




  • Get a scoop of ice cream at Emily’s Produce (featuring Scottish Highland Creamery ice cream). For a wide selection of donuts, head to Bay Country Bakery. For more bakery treats, plus breakfast, lunch (and mimosas for Mom and Dad), try Black Water Bakery.
  • Many of Dorchester County’s restaurants are family-friendly. See our Dorchester Dining Guide.
  • Give yourself a well-deserved break – and an adult beverage – with a trip to the family-friendly Layton’s Chance Winery with outdoor games and a nature trail and occasional live music.


Print Friendly, PDF & Email