Updated June 6, 2024

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, paddle a kayak, and much more. Our 2024 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 weekdays and 10am-2pm on weekends 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!

Dorchester County is also home to one of the most kid-friendly resorts in Maryland – Hyatt Regency Chesapeake Bay Resort in Cambridge – with mini golf, dive-in movies, Camp Hyatt, game room, s’mores, and more.


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

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



  • U-PICK AND MORE 1: Dig into a farm adventure and pick your own blackberries, blueberries, or wildflowers at Emily’s Produce. While you’re there, see the goats and other barnyard animals, burn off some calories at Kyle’s Farm Fields of Fun, grab lunch or indulge in a scoop of Scottish Highland Creamery ice cream. Oh, and there’s plenty of local produce, too!
  • FARM ALONG WITH EMILY: Emily’s Produce is also offering a Camp Farm Along for ages 4-8. The two-hour sessions include hands-on activities and snacks. Offered 10am-12pm on Thursdays from June 20 through Aug. 1.
  • FARM TOUR: 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.
  • U-PICK AND MORE 2: Let the kids pick flowers with wild abandon at Vintage Family Farms. Bring your own clippers. Open Thursday through Sunday in season.
  • FAIR FUN: Experience the fun of a county fair at the Caroline-Dorchester County Fair Aug. 7-10 with 4-H exhibit, barnyard exhibit, train display, animal shows, children’s day program, and more. See the schedule.
  • HORN POINT LAB SUMMER CAMP: Check out Horn Point Lab’s Kids Summer Adventures with lots of hands-on activities in July and August.
  • FARMER’S MARKET: Stop by the waterfront Cambridge Farmers Market, each Thursday 3-6pm at Long Wharf Park in Cambridge.

Skipjack Nathan of Dorchester

At the helm on the Skipjack Nathan of Dorchester.



  • SKIPJACK SAILS: 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. Most Saturdays, June through October. Reserve ahead.
  • Kayaking in Dorchester County, Maryland | Visit Dorchester

    Kayaking with Blackwater Adventures. Photo courtesy Maryland Tourism.

    PADDLE OR BIKE: 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.)

  • SEE A LIGHTHOUSE: Climb the spiral steps and enjoy the view at the Choptank River Lighthouse. Open daily for self-guided tours, 9:30-5pm with free admission.
  • WATCH FOR WILDLIFE: 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.
  • GO FISH 1: Free fishing days! In Maryland, anyone may fish without a recreational fishing license on June 1, June 8 and July 4, 2024. All other fishing regulations apply.
  • GO FISH 2: Learn to cast a line with the Mid-Shore Fishing Club at the Kids’ Fishing Derby  9am-12pm on Aug. 3 – for ages 5-12 at Long Wharf Park in Cambridge. Pre-register. Check for more info here.
  • GO FISH 3: Get the whole family signed up with a fishing charter.
  • SWIMMING: The Dorchester County Pool at 107 Virginia Ave. in Cambridge opens for the 2024 season on June 15.
  • NIGHT SKY TOURS: See the night sky in a whole new way with Blackwater National Wildlife Refuge’s Night Sky Tours, using their astronomical telescope. (Best for older kids.)
  • HORSEBACK RIDING: Ride ’em cowboy at Windy Way Horses – with lessons, painted pony events, and summer camps.


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.

  • THREE CULTURES: 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.  (For the free Audio Tour, call 410-858-4173 on your cell phone)
  • TREASURE HUNT: Go on a treasure hunt through history with the Dorchester County Passport Tour; pick up what you need at the Dorchester Visitor Center, 2 Rose Hill Place in Cambridge.
  • HARRIET TUBMAN 1: 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. Be sure to download the free Audio Guide before you head out. While you’re exploring, don’t miss the 12-foot “Beacon of Hope” sculpture (Stop #3) and the moving “Take My Hand” mural (Stop #6).
  • HARRIET TUBMAN 2: The Harriet Tubman Underground Railroad Visitor Center offers both a Junior Ranger program and, new this year, the Eastern Shore Explorers Program, offering both rural and urban expeditions and the opportunity to earn a certificate, patch, and pin! Both programs are free.
  • HARRIET TUBMAN 3: Join a walking tour with live music performing Underground Railroad code songs with a banjo player, led by the Harriet Tubman Museum & Educational Center.
  • Junior Ranger program at Harriet Tubman Underground Railroad Visitor Center

    Junior Ranger program at Harriet Tubman Underground Railroad Visitor Center.

    GHOST WALK: Call in the Ghost Busters on a Cambridge Ghost Walk along Maryland’s most haunted street (best for middle school on up).

  • BACK TO THE 1800S: 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.
  • HISTORY GALORE: 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.
  • MURALS: 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!)


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.

  • PLAYTIME! Cut loose at Cabin Fever Play Centre – the only play place and arcade on the Mid-Shore – with extensive inside play structures, MEGA Brite, Giant Connect 4 and plenty of arcade games to keep all ages happy.
  • ESCAPE ROOM, AXE THROWING: Head to DoCo Axe Co. for axe-throwing (16 and over only; closed-toe shoes a must) or have the family take on a virtual reality Escape Room (good for tweens and teens and older) or the golf simulator.
  • AT THE MOVIES: Sit back and watch movies in air-conditioned splendor at Cambridge Premium Cinemas, and check out their new upgrades (including luxury power recliners) and lower prices – $7 per person, no matter what age or what showtime. At the grand re-opening June 15, 10am-12pm, enjoy free samples of popcorn and soda, see the renovated cinema, get in on the photo ops, spin the prize wheel, and more. Get the latest.
  • BOWLING & BILLIARDS: Strike out on your own at Choptank Bowling & Billiards.
  • LIBRARY FUN: Check out the many activities – from family bingo to puzzle swap to  spoken word open mic – going on at the Dorchester County Library, at both the Cambridge and Hurlock branches. The Cambridge branch also offers a Second Saturday Book Sale, with used books available for $1 or less.


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.

    KID-FRIENDLY RESORT: 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).

  • PLAYGROUNDS: 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.
  • TRIATHLON: Sign up your youngster (ages 6-15) for the Gerry Boyle Firecracker Kids Triathlon July 4 with a fun and supportive environment for a swim, bike, and run event at the YMCA in Cambridge.



Phippin's Crafting Corner - Cambridge, MD

Hands-on fun at Prodigal Creations (formerly Phippin’s Crafting Corner). Photo courtesy of Prodigal Creations.



  • Get your hands dirty with 450 different projects and classes at the community crafting studio of  Prodigal Creations (formerly Phippin’s Crafting Corner) in Cambridge. See the upcoming classes. All are invited to their grand opening June 22 at 9am.
  • Kids are welcome to make a mess in the kitchen at Little Whisks Culinary School for kids, hosted by Mandala Pies. The next one is June 30 at 10am – Fruit Popsicles & Pizza at their bakery in Vienna.
  • The Dorchester Center for the Arts offers a few ways to flex your creativity. Check out upcoming classes and workshops. There’s also Art in the Community every Wednesday at 5:30pm through June 19. Presented by Groove City Back Heritage & Culture Group with food, music, arts, field trips, door prizes.


Fireworks in Cambridge, MD - Photo by Jill Jasuta – Dorchester County

Spectators watch the fireworks in Cambridge, MD. Photo by Jill Jasuta.


DADS & DAUGHTERS: One Mission Cambridge hosts a Father Daughter Dance June 13, 5-8pm with dancing, DJ, princess craft corner, face painter, raffle, snacks. At 447 Venue in Cambridge. Buy tickets.

READS & RIDES: R&M Performance and Appleseed Books host a fun time with story time, snacks, and a tour of their 60,000-square-foot shop with 80 cars to see June 17, 10:30-11:30am. Space is limited. Register.

BOOM! Watch the July 4 fireworks over the Choptank River in Cambridge. The best viewing is at Gerry Boyle Park at Great Marsh (1 Somerset Ave. in Cambridge), Long Wharf Park, High and Water Streets), and next to the Dorchester Visitor Center (2 Rose Hill Pl.). Fireworks generally start at dusk, around 9:15pm. Bring your own chairs or blankets and snacks. Free!

READ: Reading Social is a free event that encourages reading for kids from birth to age 12. Runs from 10am to 12pm on first Saturdays in Cambridge; second Saturdays in Hurlock. The focus is on improving literacy and building home libraries for children. During the time the children are here, they will receive a healthy snack, reading support, and an art activity.

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 South Mountain 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.


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