Family Fun Guide - Summer 2025 - Heart of the Chesapeake

May 30, 2025 • Food & Drink • Outdoor Activities

2025 FAMILY FUN GUIDE FOR DORCHESTER COUNTY, MARYLAND

Updated June 16, 2025

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!

At the helm on the Skipjack Nathan of Dorchester.

OUTDOOR ADVENTURES

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. Plus sunset sails June 27, July 11, 18, 25. Reserve ahead.
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 2: Free fishing days! In Maryland, anyone may fish without a recreational fishing license on June 7, June 14, and July 4. All other fishing regulations apply.
GO FISH 3: Get the whole family signed up with a fishing charter.
SWIMMING, TAKE 1: The Dorchester County Pool is located at 107 Virginia Ave. in Cambridge. Open daily 12-6pm, but closed on federal holidays. Check the Facebook page for special events. For questions, call 410-228-5578.
SWIMMING, TAKE 2: If you're planning to swim in the Choptank River, check out the weekly SwimGuide from ShoreRivers, with their weekly bacterial monitoring results.
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.

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

FARMS AND CRITTERS

U-PICK AND MORE 1: Dig into a farm adventure and pick your own berries and 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!
U-PICK AND MORE 2: Let the kids pick flowers with wild abandon at Vintage Family Farms in Hurlock. Check on their opening status on Facebook or Instagram.
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.
FARM LEARNING: Join Farm Along with Emily's Program at Emily's Produce. For ages 4-6. Each two-hour session covers a farm-related topic with plenty of interactive fun. Weekly sessions begin June 25. Find out more and register.
FAIR FUN: Experience the fun of a county fair at the Caroline-Dorchester County Fair Aug. 6-9 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. Horn Point Lab also offers a behind-the-scenes tour on Tuesdays at 10am until Labor Day. Best for age 10 and older.
FARMER'S MARKET: Stop by the waterfront Cambridge Farmers Market, each Thursday 3-6pm at Long Wharf Park in Cambridge.

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

STEP INTO THE TIME MACHINE

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 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, often with live music performing Underground Railroad code songs with a banjo player, led by the Harriet Tubman Museum & Educational 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. They also host fun events.
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!)

Arcade at Cabin Fever Play Centre.

WHEN YOU’D RATHER BE INSIDE

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. New this year: a sensory room for those who need a quiet break. Don't miss the chance to Play with Bluey on June 29 - it will sell out fast!
AT THE MOVIES: Sit back and watch movies in air-conditioned splendor at Cambridge Premium Cinemas, and check out their upgrades (including luxury power recliners) and lower prices – $7 per person, no matter what age or what showtime and $7 for bottomless popcorn/soda. Plus, Camp Flagship: Summer Family Films brings five weeks of family films on Fridays, Saturdays, Mondays and Wednesdays at 10am starting July 11 with $2 tickets and $4 kid trays. Advance tickets recommended. Get the latest.
BOWLING & BILLIARDS: Strike out on your own at Choptank Bowling & Billiards. They're hosting some Kids Bowl Free days this summer; check their Facebook page for the latest.
LIBRARY FUN: Check out the many activities – from family bingo to puzzle swap to the Anime Club – going on at the Dorchester County Library, at both the Cambridge and Hurlock branches.

Playground at Sailwinds Park East, Cambridge, MD

BURN OFF SOME ENERGY

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.

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

HANDS-ON CREATIVITY AND ENTERTAINMENT

FLEX YOUR CREATIVITY with the Dorchester Center for the Arts. DCA is offering the Greg Leonard Creative Camp for Young Artists – a FREE four-week art intensive July 7-11 for grades 9 through 12. There are a range of other classes and camps throughout the summer covering drawing, clay, potter's wheel, and more. See the offerings. Or mix art with movement with Fit & Fun, a free family yoga and art program at the Hurlock Public Library July 2, 9, 16, 23. Register at 410-943-4331.
GET YOUR HANDS DIRTY with crafting projects and classes at the community crafting studio of Prodigal Creations (formerly Phippin’s Crafting Corner) in Cambridge. See the upcoming classes.

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

FUN & FESTIVE

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!

Donuts galore at Bay Country Bakery in Cambridge.

REFRESHMENT & TREATS

ICE CREAM & MORE! The ice cream scene in Dorchester County has changed a lot this season. Here's the latest:
> Try homemade hand-dipped ice cream from the Frozen Farmer at Chilly Billy’s, 600 Roslyn Ave., Cambridge (across from Dunkin' Donuts, in a truck located in the Citgo parking lot).
> Indulge in a scoop of farm-fresh South Mountain Creamery ice cream and other frozen treats at Emily’s Produce. Open Monday and Wednesday–Friday 9am-6pm; Saturday and Sunday 9am-5pm.
> Stop by Groove City Sweets & Treats for more than two dozen flavors of hand-dipped Hershey's ice cream, 601 Pine St., Cambridge. Open Tuesday–Sunday, 2-8pm.
> JAHA Ice has Western Shore-style snowballs on the Eastern Shore. The mobile cart has more than two dozen flavors of specialty shaved ice. Their home base is 308 N. Main St., Hurlock, but see where they're serving this week.
> Lil Bitta Bull BBQ is now offering soft-serve ice cream – everything from a classic vanilla cone to a loaded sundae to a Nor’Easter. 2839 Ocean Gateway, Cambridge. Open Wednesday and Thursday, 2-8pm; Friday–Sunday, 11am-9pm.
> Enjoy hand-dipped Hershey's ice cream at the Scoops ice cream truck run by Simmons Center Market, 600 Race St. Cambridge. Check their Facebook page to see if they're on the move. Usually serving up Friday, Saturday, and Sunday.
DONUTS & MORE: For a wide selection of donuts, head to Bay Country Bakery. For more bakery treats (homemade PopTarts!), plus breakfast, lunch (and mimosas for Mom and Dad), try Black Water Bakery.
FAMILY-FRIENDLY DINING: Many of Dorchester County’s restaurants are family-friendly. See our Dorchester Dining Guide.
FAMILY-FRIENDLY WINERY: 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.