Summertime spells freedom and fun! It’s time to work on that summer bucket list and head out on adventures that will thrill you, enlighten you, and create beautiful memories that will last a lifetime. In a visit to Dorchester County, Maryland, you can do all of this and more.

Get Crackin’ with a Crab Feast

No summertime bucket list for Maryland’s Eastern Shore would be complete without checking off a Chesapeake Bay crab feast. The crabs are at their most bountiful in the summer and early fall months, so the timing is perfect. If you want to dine in at a sit-down restaurant, either indoors or outdoors, Ocean Odyssey in Cambridge or Suicide Bridge Restaurant in Hurlock are the perfect places to sink your teeth into this tasty tradition.

Prepare to get messy as those steaming hot, crimson crabs arrive before you. Break into these delicious delicacies to find the sweet, juicy crabmeat inside that everyone raves about. Dip it in drawn butter, drag it through zesty Old Bay seasoning, or just enjoy it plain. Wash it all down with a mug of cold beer or iced tea.

If you’re looking to enjoy the crabs at your Airbnb, or to dine on them al fresco at a public park like Gerry Boyle Park at Great Marsh or Long Wharf Park, both in Cambridge, there are several seafood retailers and restaurants that offer to-go steamed crabs. No matter where you choose to devour it, it will be a meal you won’t soon forget.

Climb a Lighthouse

Choptank River Lighthouse in Cambridge, MD - Photo by Jill JasutaIf you’ve ever dreamed of being a lighthouse keeper, or you just want to take in the view from outside of the lantern room, then head to the Choptank River Lighthouse on the waterfront in Cambridge. A charming landmark that rises above the Choptank River commanding attention and admiration, the Choptank River Lighthouse is a replica of its predecessor that guided mariners along the Choptank River for generations. It was built in a screwpile style, characteristic of other lights on the Chesapeake Bay, and it features a hexagonal house. The red tin roof that tops both levels of the lighthouse creates a beautiful contrast against the white house and a summery blue sky. The lighthouse is open daily, May through October, 9:30am-5pm, and there are docents on weekends.

Visits to the lighthouse are free, but donations are kindly encouraged. Kids especially enjoy trips to the lighthouse, as they are intrigued by the tiny winding stairs that lead to the second level. Be sure to pause for a breath of fresh air at the top and take in the views of the river and the Cambridge waterfront. Visit the small museum on your way out and learn more about the back story of the lighthouse and local maritime culture.

Sip Strawberry Wine

Layton's Chance Winery – Dorchester County, MDThe pace of summer is supposed to be slow, and nothing spells leisure like sitting in a rocking chair, looking out over a vineyard, and sipping on a refreshing adult beverage, whether a glass of rosé or a wine slushie. At Layton’s Chance Vineyard and Winery in Vienna, that’s exactly what you can do.

For more than a decade, William and Jennifer Layton have opened up their beautiful farm to Dorchester County locals and visitors to provide a place to unwind and enjoy, not only their 20 types of homegrown wines – including fruit-based wines made with local produce (“like summertime in a bottle”) – but a taste of the good country life, too. Layton’s Chance is also the Mid-Atlantic’s first craft winery!

Sit inside the tasting room or outside on the porch, kicking back in a circle of Adirondack chairs or sipping your wine at a table beneath the vine-covered pergola. You can also take a tour of the winery on Saturdays and Sundays at 1pm or 3pm, or meander the paths in the vineyard.

This family-friendly venue is great for kids, too, as there is a playground and yard games to keep them occupied and happy while you relax. There is also a stage for live music throughout the summer (see what’s coming up).

Get Out on the Water

Sunset Sail on the Skipjack Nathan of Dorchester in Cambridge, MDMake it a different kind of on-the-water experience with a dollop of local culture. Join a public sail on the Skipjack Nathan of Dorchester, an authentic oyster-dredging boat. (The skipjack is Maryland’s state boat!)

Honoring the watermen heritage of the region, the Nathan offers public cruises on most Saturdays on the Choptank River. Visitors can help raise the sails or even take their turn at the helm. Kids of all ages love the hands-on experience they get on the Nathan, and the views of the river from the boat are spectacular.

The docents are passionate about the history of the area and its skipjacks, so they are able to captivate their passengers with stories of local maritime history. Passengers young and old are fascinated when they pull up the dredge to demonstrate how oysters are caught, which is often an exciting experience as crabs and other creatures make an appearance.

Pamper Yourself

Hyatt Regency Chesapeake Bay Resort, Cambridge, MarylandIf treating yourself to a much-needed weekend of pampering is high up on your summer bucket list, then head to the Hyatt Regency Chesapeake Bay Resort in Cambridge during your Dorchester County vacation.

This 342-acre waterfront resort has it all, and everyone in the family will find something to indulge in. Whether it’s hitting the 18-hole, picturesque, riverfront golf course or taking a dip in the lavish outdoor pool or hot tub, you’ll be impressed by the luxurious amenities amid such a beautiful natural backdrop.

Enjoy s’mores at the outdoor fireplace before bed and wake up to breathtaking views of the Choptank River. And if it’s classic pampering you’re looking for, rejuvenate and restore your mind, body, and soul with an array of treatments and massages at Sago, the resort’s spa, that will have you radiating that summer vacation glow.

See Wild Bald Eagles Up Close

Eagle at Blackwater - photo by Ron KetterImmerse yourself in the wild and beautiful outdoors and discover landscapes, dramatic waterscapes, and wildlife – including bald eagles. Blackwater National Wildlife Refuge, located 12 miles south of Cambridge, has one of the greatest number of bald eagles on the East Coast, north of Florida. See them perching in loblolly pine trees or soaring overhead.

For an opportunity to view one of these regal birds – or great blue herons, egrets, red-winged blackbirds and more – in their natural habitat, you have a few choices of how you can explore the refuge. One option is to take the 4-mile Wildlife Drive, a paved road that meanders along the Blackwater River and offers exceptional views of the refuge. Go by car, by bicycle, or on foot. If you’re feeling a little more adventurous, launch a kayak into one of the three water trails that will take you by cordgrass, cattails, marsh hibiscus, and fragrant waterlily. Another way to explore the refuge is by way of one of four land trails. Venturing into such unspoiled, wild beauty is rewarding, but don’t forget the bug spray! No matter how you decide to explore Blackwater National Wildlife Refuge, you will have the privilege of getting to experience what the Nature Conservancy calls one of the “Last Great Places.”

Go Flower Picking

Sunflower Spectacular at Emily's Produce, Cambridge, MDWithin a few minute’s drive from Cambridge is Emily’s Produce, owned and operated by a seventh-generation farming family – a must-stop for locals and visitors alike in Dorchester County. The store offers homegrown fruits and vegetables,  fresh local meats, jams, baked goods and treats, ready-to-eat foods, ice cream (from Scottish Highland Creamery, an Eastern Shore icon), and more. It’s the perfect place to bring the kids to enjoy a hand-dipped cone and a romp around the play area, but visiting with the chickens, pigs, and goats is a proven favorite of kids of all ages. More than just a farmers market, however, Emily’s is a Maryland Eastern Shore staple.

There are also various U-Pick opportunities throughout the season, including blueberries,  blackberries – and flowers from their wildflower field. Emily’s also hosts fun events that combine elements of farming and food. See what’s coming up.

North of Cambridge is Vintage Family Farms, a flower farm in Hurlock with U-Pick flowers Thursday through Sunday. BYOC (Bring Your Own Clippers)!

Discover a Real-Life Hero

Tubman Visitor CenterDrive another 10 minutes down the road from Emily’s Produce and you’ll discover the Harriet Tubman Underground Railroad Park and Visitor Center in Church Creek. Here you will learn about the incredible life and triumphs of Harriet Tubman, the heroic abolitionist who was born in Dorchester County and who escaped slavery – then returned 13 times to lead more than 70 others to freedom. Through thoughtfully constructed exhibits, the visitor center brings the world-renowned story to life in a way you will never experience anywhere else.

Or plan a narrated walking tour in Cambridge with the Harriet Tubman Museum & Educational Center – which often includes live music sharing some of the code songs that were used along the Underground Railroad.

See History in a New Way

If gaining new perspectives and knowledge is on your list of adventures you’d like to take away from your summer vacation, then visiting Handsell Historic Site in Vienna is going to captivate you. Learn the stories of three different cultures – Native Americans, colonial settlers, and free and enslaved Blacks – that overlapped here over the course of 400 years, each leaving behind their own traces of existence.

Handsell House in Dorchester County, MD; photo by Abby StewartAccording to legendary explorer Captain John Smith in 1608, an “emperor” oversaw the largest Native American village he would encounter, there on the grounds of Handsell, which appeared to be the tribe’s capital.

Over the next 400 years, the lands around Handsell would be the location of a British invasion, followed by an African American inhabitancy of both enslaved and free people.

Take a tour of the brick Handsell house, dating back to the 1700s, on Saturdays between 11 am and 3pm during their Summer Saturdays through Labor Day. Most of the Saturdays include special programming or hands-on workshops.

You can also explore the Chicone Indian longhouse – the first such longhouse to be built on the Eastern Shore in 200 years, using traditional materials and techniques. If you miss the Saturday house tour, you’re still welcome to wander the grounds daily from sun-up to sun-down and experience the melding of these three cultures through an audio tour, interpretive signs, and more.

There is so much to do and see in Dorchester County at any time of year, so be sure to create your next traveling bucket list and return to see in what creative, exciting, and memorable ways you can check those new adventures off.


Things to Do With Your Kids This Summer

Find plenty of family-friendly outdoor adventures, interesting hands-on experiences, and fun with kids in Dorchester County! 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.

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