As far as Eastern Shore towns go, Cambridge might not get the same attention as say St. Michaels, or you may think of it more as a pit stop on the way to a destination like Ocean City. But Cambridge has so much more to offer than that.
Nestled along the banks of the Choptank River in Dorchester County, Cambridge, founded in 1684, is one of the oldest colonial cities in the nation. With a charming and walkable downtown, a thriving waterfront, and plentiful history, this Eastern Shore town should be on everyone’s bucket list.
History and Nature Collide
If exploring by car, before heading into town, I recommend driving for about 15 minutes more until you get to the Harriet Tubman Underground Railroad Visitor Center. This is where you should start your visit—by revisiting the past and learning about the history that shaped the region.
Harriet Tubman was born into slavery in 1822 in Dorchester County. In 1849 she escaped to Philadelphia, but her own freedom wasn’t enough. She returned to Maryland time and time again using the Underground Railroad, various safehouses in which abolitionists provided sanctuary for freedom seekers. “Conductors” led the journeys to freedom, while “Station Masters” hosted freedom seekers within their homes, churches, or other safe spaces. Tubman, known as the “Moses of her people,” is the Underground Railroad’s best-known conductor. Before the Civil War, she repeatedly risked her life to guide 70 enslaved people north to new lives of freedom.
The Harriet Tubman National Historical Park preserves the same landscapes that Tubman used to carry herself and others away from slavery. One of the most interesting things for me as a modern-day visitor is that many of the landscapes surrounding the park look much as they would have in Tubman’s time. The visitor center is a perfect launching point for learning about this amazing woman, featuring immersive exhibits about her life and daring rescue missions, as well as a theater that truly brings the story to life.
At the visitor center, be sure to grab some literature or scan the QR code on the front desk for a map that details the Harriet Tubman Underground Railroad Byway. The byway is a self-guided driving tour that winds for more than 125 miles through the beautiful landscapes and waterscapes of Maryland’s Eastern Shore and another 98 miles through Delaware. It includes 45 historically significant sites related to the Underground Railroad. You could easily spend an afternoon or a couple of days exploring all of the sites. Because we were short on time, we visited just two stops that were closest to the visitor center: Brodess Farm, where Tubman was born, and the Bucktown General Store, an authentic early 19th century store that has been preserved to appear much as it did in Tubman’s time. It was the site of Tubman’s first act of defiance that would later lead to her eventual escape from slavery. The store is open for tours by appointment only, but even without one it’s well worth the stop to view the exterior.
Visit nps.gov/hatu and harriettubmanbyway.org for more information.
While on the byway, it’s just a short drive to Blackwater National Wildlife Refuge, often referred to as the “Everglades of the North.” Established in 1933, the site is a waterfowl sanctuary for birds migrating along the Atlantic flyway. It is one of the chief wintering areas for Canada geese and home to the largest breeding populations of American bald eagles on the East Coast north of Florida. The refuge is also home to the largest natural population of the formerly endangered DelMarVa peninsula fox squirrels.
Blackwater features more than 20,000 acres of rich tidal marsh, mixed hardwood and loblolly pine forests, managed freshwater wetlands, and croplands. There are over five miles of hiking trails and 17 miles of paddling trails, along with the 3.6-mile Wildlife Drive, all of which provide ample opportunities for seeing wildlife up close in their native habitats. The area is popular with photographers, birders, and cyclists. All public areas outside of the Wildlife Drive, including the visitor center, are free of charge. A daily vehicle pass costs $2.50 and only $0.50 for pedestrians/cyclists. To learn more, visit fws.gov/refuge/blackwater.
Maritime Heritage
After spending the first part of your day immersed in landscapes that are pretty much unchanged from Tubman’s time, a pretty miraculous feat in this day and age, it’s time to head to downtown just a short drive away.
The town’s rich maritime heritage is still very evident today. From boatbuilding to watermen, the past and the present go hand in hand. Much of this can be explored at the Richardson Maritime Museum, which aims to preserve and promote the region’s maritime history.
From the maritime museum, head across the Cambridge Creek Drawbridge and make a right onto High Street. I recommend finding parking towards the top of the street and walking the short distance to Long Wharf Park. High Street is a brick-paved historic district featuring 18th to 20th century architecture including Federal and Victorian homes. One such home on this street, the Bayly House, is thought to be the oldest dwelling in Cambridge, dating back to the 1740s. The street is a delight to stroll down, marveling at the historic homes. It was designed in the typical colonial fashion, meaning that it leads from the waterfront to the highest point, where the church was placed, to avoid flood zones.
At the bottom of the street you’ll find Long Wharf Park, home to the skipjack Nathan of Dorchester. Commissioned in 1994, she was funded by contributions and built by volunteers as a way to preserve the wooden boat building technology and nautical heritage of the region. The skipjack is the Maryland State boat, and Dorchester County led all others in the number of skipjacks built. Public sails and custom charters are offered seasonally. Visit skipjack-nathan.org to learn more.
Also located at Long Wharf Park is the replica Choptank River Lighthouse, modeled after a historic screwpile lighthouse that once guided mariners along the Choptank River. The lighthouse is open daily from May through October. There is no admission charge, but there is a donation box. If it’s not open during your visit, you can still walk out along the docks to see it up close.
Vibrant Downtown
By this point you’ve probably worked up an appetite, and you’re in luck, because there are plenty of options downtown from bakeries to a pizzeria and wine bar and a brewery. If you click to visitdorchester.org/eat-and-drink and filter for ‘Cambridge,’ you can find a great list of options, so we won’t list them all here. But there is one place I want to give a special shoutout to: The Dive Club, which is from the folks at RAR Brewing, a Cambridge staple.
This immersive nautical themed restaurant is quite the experience. It opened roughly two-and-a-half years ago, and everything from the décor to the drinks is so carefully designed and on-theme that it’s easy to forget you’re not actually on the high seas.
The booths feature portholes and barnacles on the walls (remember when I said no detail was too small?). There’s a skeleton sitting at the end of the bar, and every so often there’s even a storm with thunder and lightning. The elaborate and delicious cocktails are tiki themed, and you’ll also be happy to find some familiar staples and of course RAR beer. The food is equally delicious; their specialty is small plates, and I can personally vouch for the make-your-own tuna poke rice bowl. Reservations are recommended at rarbrewing.com/location/the-dive-club. Visit PropTalk’s YouTube channel to check out a fun video of our experience.
The Visit Dorchester website is also a great resource for a list of shops and other sites of interest in town. From antiques stores to art galleries and boutique shops, there is no shortage of things to see and do.
One of the reasons Cambridge is so special is its ability to weave its past into the present. As a visitor, being able to travel from a modern and happening main street to landscapes that have been practically unchanged for over 200 years in just 20 minutes is remarkable. Whether visiting by car or by boat, it seems there will always be something new to discover.
By Kaylie Jasinski