- Located 13 miles up the Choptank River from the Chesapeake Bay
- Settled in 1684 and named for the English university town in 1686
- Home to the Harriet Tubman Museum and Mural, and a key stop on the Harriet Tubman Byway
What Makes It Unique
Cambridge is one of the earliest English settlements on the Chesapeake, but the town was hit by several devastating fires during its long history. The area took another major hit in the mid-1960s when Phillips Packing Company (Cambridge’s biggest employer) closed. But during the decades that followed, the citizens of Cambridge worked hard to bring the town back with new businesses, museums, restaurants and all the other things that attract happy visitors. Today, its protected basin and deep-water creek make it ideal for boaters who want to stroll the tree-lined streets dotted with lovely old homes and walk to great restaurants. Soak up its unique history at Long Wharf and Ruark Boatworks, and take in the tributes to its hometown heroine, Harriet Tubman, who is justly honored with a museum, stunning murals and a national historic trail that traces her life and movements in Cambridge and through the neighboring Dorchester County countryside.
The entrance to the Choptank River is about 23 miles south of the Bay Bridge. It is then about 13 miles upriver to Cambridge. You can cut off a few miles by taking the Knapps Narrows cut-through near Tilghman Island, which is a shortcut from the Bay to the Choptank. It has a controlling depth of 8 feet, and gives you a chance to travel through what has been called the busiest drawbridge in the world.
If you are coming from the Norfolk area, you’ll find the entrance to the Choptank about 100 miles up the Bay. Either Deltaville or Crisfield would make a good stop along the way. From Deltaville, the Choptank is about 65 miles.
Cruise up the Choptank River as far as green 25, the last marker before the U.S. 50 bridge, and then either head for Cambridge’s municipal yacht basin or find the markers 1 and 2 for the entrance channel to Cambridge Creek. The other, equally delightful option is to keep going under the bridge (sailboats beware, the vertical clearance is only 50 feet) and dock at the Hyatt Regency’s marina.
If you are coming by car, you will find Cambridge just off of U.S. 50; you’ll know you’re there by the sail-shaped awning of the visitors pavilion on the southeast side of the Choptank River bridge. From the Baltimore area, it’s about a 90-minute drive via the Chesapeake Bay Bridge. From the Norfolk area, it’s a three-hour drive, taking the Chesapeake Bay Bridge-Tunnel and U.S. 13 to Salisbury, then U.S. 50 the rest of the way.
If you want to be within walking distance of nearly everything in town, take a slip inside the breakwater at the Cambridge Yacht Basin, managed by Oasis. Or better yet, try the Cambridge Yacht Club, which shares the basin with the city marina and usually has some slips that are open to visitors. (They also have reciprocity for members of Chesapeake Bay Yacht Club Association clubs.) The farmers market and Long Wharf events, as well as the Choptank River Lighthouse, are short walk along Water Street, and restaurants, shops and museums will be a little longer walk up High Street.
If you like the idea of anchoring out or tying up to the town’s free dock, follow the channel into Cambridge Creek, one of the Chesapeake’s deepest and a key reason for the town’s long success as a port. On the way in, you’ll pass Yacht Maintenance Company, then the turning basin. Here you’ll find J.M. Clayton Company Seafood, immediately to the right. The company was founded in 1890, is still family owned, and is said to be the oldest working crab processing factory in the world. On the adjoining wall you’ll find the free bulkhead, behind several Dorchester County office buildings. There are plenty of cleats, but be very careful to protect your boat from the long bolts that stick out from the bulkhead in several places. If you prefer to anchor, be sure to allow plenty of room for J.M. Clayton’s crab boats.
Also try Generation III Marina, which is located at the head of the creek; it has a depth of 8- to 12-feet and slips for transients or anyone needing repairs. Cambridge is a big town for both recreational and commercial boating, and the Wheatley family is known for fine craftsmanship and attention to detail in all types of service, which has earned them a loyal following over 30 years in business.
River Marsh Marina/Hyatt Regency Chesapeake
If you’re looking to be spoiled, then the marina at the Hyatt Regency Chesapeake Bay Marina (or the Hyatt Regency itself) is for you. You could treat this one as a separate destination altogether, but it’s easy to get to downtown Cambridge from here.
By boat, simply continue under the U.S. 50 bridge (remember that 50-foot vertical clearance, sailboats) to green 27. From there, point south and you’ll see the marina’s breakwater, with the entrance facing the downriver side. The marina has all the usual amenities, though they are a bit of a walk, and the added resort fee gives you access to everything the hotel complex has to offer.
Staying on Land
The Cambridge House Bed & Breakfast is a circa-1847 former sea captain’s home on High Street with six period bedrooms, a lovely garden lily pond and an outdoor hot tub.
The Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina is a destination in its own right. This sprawling, AAA Four Diamond resort has everything you need for a weekend away, with 400 newly renovated rooms (all with balcony or balconette), a pool and waterslide, 18-hole golf course and the elegant Water’s Edge Grill. The airy atrium bar Michener’s Library is the perfect place for to take it all in with a cocktail. And they welcome dogs with a one-time $150 charge.
Exploring by Water
There is an excellent launch area with plenty of overnight parking at the Franklin Street Boat Ramp. Here you’ll find two docks, four ramps and a breakwater to launch directly into the Choptank. Nearby Trenton Street Boat Ramp is much smaller but will launch you into Cambridge Creek. Neither requires a use permit. North of town, you can launch at the Gerry Boyle Park at Great Marsh boat ramp.
The period-correct skipjack Nathan of Dorchester was built by volunteers in 1994 in homage to the unique wooden vessels used for centuries to dredge oysters on the Bay. Join her on a Saturday for a two-hour sailout into the river and learn how watermen would work the Bay from these unique vessels, where were named the state boat of Maryland in 1985.
Just 12 miles from Cambridge, Blackwater National Wildlife Refuge is a natural sanctuary established in 1933 to protect migratory wildfowl along the Atlantic Flyway. Bring your own kayak or SUP, or join Blackwater Adventures Chesapeake Bay for guided paddle tours of waterways that wend through the landscape. Blackwater has a full array of rental vessels, as well as bicycles, and they can deliver equipment with prior reservation.
Exploring by Land
Just downstream of the U.S. 50/Choptank River Bridge, the short but deep Cambridge Creek divides the town in two. Most of the old town, with its oldish buildings, newish restaurants, Long Wharf, and the municipal marina and yacht club, are located on the west side of the creek. The leafy residential streets are lined with fine old houses, while the main part of downtown can be found a few blocks inland. If you walk up High Street (which begins at Long Wharf) and then turn left onto Poplar Street you’ll find yourself right in the center of things. Continuing on, Sailwinds Park and Visitor Center, Ruark Boatworks (part of the Richardson Maritime Museum) and more businesses can be found within a short walk to the east of the creek.
Like many towns on the Chesapeake, the water dominated the economy for centuries, and Cambridge, with its deep-water creek, served as the main port for the surrounding area. It was here at Long Wharf that tobacco, tomatoes, and yes, agonizingly, enslaved people, came and went. Today, crab boats continue to pass by Long Wharf on their way into Cambridge Creek to J.M. Clayton Seafood, whose crabmeat is sold all over the country. Step inside Choptank River Lighthouse to see artifacts of the Bay’s lighthouse culture and get a good view.
The free, downloadable Visit Dorchester Audio Tour Guide app is a great way to discover more of the town’s quirks, including the fraught history of the Dorchester County Courthouse, and the house where sharpshooter Annie Oakley and her husband briefly lived. And you’ll learn about Groove City, the name given to the Pine Street neighborhood where Ella Fitzgerald, Count Basie and Duke Ellington came to play. The third tour gives fascinating stories about all the murals on the Chesapeake Mural Trail, including the viral mural that depicts Harriet Tubman with her arm outstretched, which is on the Harriet Tubman Museum & Education Center on Race Street.
On the other side of Cambridge Creek, Richardson Maritime Museum is closed for work, but you can still get a look at the restoration work they’re doing over at Ruark Boatworks, a celebration of the Eastern Shore’s long and colorful history of boatbuilding. You’ll see volunteer boatwrights building and restoring the Chesapeake’s iconic watercraft, including the skipjack, pungy schooner and log canoe.
RAR Brewing is a national success story that began here. They make excellent beer (try the Nanticoke Nectar IPA) and do great dogs and burgers out of their side restaurant Chessie Burger. Then head across the street where retro speakeasy Blue Ruin specializes in the lost art of creative cocktails, with over 150 on the menu, paired with small plates. Vintage 414 is part wine bar (with beer and cocktails too), part restaurant (flatbreads and cheese boards) and gourmet food shop.
Portside Seafood Restaurant has been serving fresh seafood overlooking Cambridge Creek for 25 years. Cambridge is home to two popular restaurants you may know from St. Michaels: Ava’s Pizzeria & Wine Bar and Theo’s Steaks, Sides & Spirits. Ava’s offers fantastic brick-oven pizza, while Theo’s has steaks and more. Harriet’s Homemade Ice Cream & Cakes is a sweet new addition to town. Maryland Blue is located waterside in nearby Madison, well worth the trip by boat or car.