Story by Abby Stewart

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.

Have a Maryland Blue 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 and the opportunity to experience this quintessential Maryland meal is plentiful in Dorchester County. 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, as Maryland crabs are delectable enough to be enjoyed just as they are. Wash it all down with a mug of cold beer or iced tea and happily check a crab feast off of your list.

If you’re looking to enjoy the crabs back at your Airbnb, or to dine on them al fresco at a public park like Sailwinds at the Dorchester Visitor Center 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 from the 1870s to the 1960s. 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 the glistening, blue water of the Choptank River.

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 museum on your way out and after you leave, enjoy a nice picnic in Long Wharf Park, located just a few feet after you step off of the dock, to relish in a different perspective of the lighthouse.

Sip Strawberry Wine

The 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 strawberry wine. At Layton’s Chance Vineyard and Winery in Vienna, that’s exactly what you can do. According to owner Jennifer Layton, they don’t just sell wine, they sell relaxation.

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, but a taste of the good country life, too.
Layton’s is also the Mid-Atlantic’s first craft winery!

In a rustic barn-like building, the tasting bar, gift shop and event space flow openly from one room into the other. The space is adorned with wine barrel tables and vintage furniture, giving it a modern farmhouse feel. Outside on the porch, kick back in a circle of Adirondack chairs or sip your strawberry wine at a table beneath the vine-covered pergola. You can also take a tour of the winery on Saturdays and Sundays at both 1pm or 3pm, walk the paths in the vineyard, and take stunning photographs surrounded by the luscious grape vines.

This family-friendly venue is great for kids, too, as there is a playground and an outdoor volleyball court to keep them occupied and happy while you relax. There is also a stage for live music or VIP tastings if you come at the right time. The Laytons invite you to come to the farm to kick back, relax, sip that strawberry wine, and check the experience off of your summer bucket list.

Go Sailing

Sunset Sail on the Skipjack Nathan of Dorchester in Cambridge, MDHave you always wanted to go sailing, or have you ever been interested in learning how an oysterman harvests his oysters? Well, on the Skipjack Nathan of Dorchester, you can experience both.

Built to continue wooden boat building techniques and to honor the watermen heritage of the region, the Nathan offers public cruises on most Saturdays on the Choptank River, where 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 either stay at or visit 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 a glass of wine by the outdoor fireplace before bed and wake up every morning to breathtaking views of the Choptank River. And if it’s classic pampering you have on your summer bucket list, 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

Bald EagleIf your summer bucket list includes immersing yourself in the wild and beautiful outdoors to discover landscapes, wildlife and foliage that you’ve never seen before, then Dorchester County is the place to be. And if seeing bald eagles in the wild is an item on that list, then Blackwater National Wildlife Refuge, located 12 miles south of Cambridge, is where you should head.

Blackwater is the epicenter of the greatest number of bald eagles on the East Coast, north of Florida, and sightings are almost guaranteed throughout the year. They make their nests in the tall loblolly pines you’ll see along the Wildlife Drive and they will often be seen soaring overhead or swooping in close. For an opportunity to closely view one of these regal birds in its 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 that offers you exceptional views of the refuge, and off of which the loblolly pines are clearly visible. If you’re feeling a little more adventurous, launch a kayak into one of the three water trails that will take you through cordgrass, marsh hibiscus, and fragrant water lilies. 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,” making it an excellent item to add to anyone’s summer vacation bucket list.

Go Flower Picking

Sunflower Spectacular at Emily's Produce, Cambridge, MDWithin just a few minute’s drive from Cambridge, you will come across Emily’s Produce, owned and operated by a seventh-generation farming family, that is a must-stop for locals and visitors alike in Dorchester County. The store offers homegrown fruits and vegetables, fresh local meats, jams and ready-to-eat foods, among other exciting farm finds. It’s the perfect place to bring the kids to enjoy a hand-dipped ice cream cone and a romp around the play area, but visiting with the bunnies, 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.

Although the U-Pick berry season has ended for the season, you can still enjoy the Sunflower Spectacular and pick beautiful, vibrant flowers from their fields. It’s an activity you can share with all members of your family to create joyous memories and start a family tradition you can all look forward to every year.

Discover a Real-Life Hero

Tubman Visitor CenterAfter checking berry picking off of your summertime bucket list, you’d be remiss not to continue your drive another 10 minutes down the road to 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 before she returned to lead 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. If discovering a real-life hero wasn’t already on your summer bucket list, it’s likely you will add it after such a moving and enlightening visit to the Harriet Tubman Underground Railroad Park and Visitor Center.

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 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 StewartHandsell House is unlike any other, and is one of Dorchester County’s most intriguing historic structures. Efforts to restore this 18th century home have only been underway since 2005, but since then, with each new piece of evidence discovered, an unusually fantastic story emerges. One where, over the course of 400 years, three different cultures intertwine in one location, each leaving behind their own traces of existence.

According to legendary explorer Captain John Smith in 1608, an “emperor” oversaw the largest Native American village he would ever encounter, there on the grounds of Handsell, which appeared to be the tribe’s capital. Over the next 400 years, that very site would be the location of a British invasion, followed by an African American inhabitancy of both enslaved and free people, all occupying the same piece of land and leaving behind pieces of their stories, weaving a tapestry of three different cultures through the fabric of time.

Take a tour of the brick Handsell house, dating back to the 1700s, on Saturdays from 11 am-3pm in the summer through Labor Day, with special programs most Saturdays. 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.

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