Downtown Cambridge is now retro-cool. The town held onto buildings from the “Mad Men” era and now has a mix of unique boutiques, art galleries and antique stores. There are a few empty storefronts, but the main street is buzzing with a number of restaurants and a regionally famous brewpub.

Cambridge is also historic — home of Harriet Tubman — and has a beautiful waterfront at the edge of town on the Choptank River although the older, historic section of town is along Cambridge Creek, a large tributary that flows into the Choptank. It was originally part of the Choptank Indian Reservation of 1669, but was named a port of entry in 1684. Now, Cambridge is one of the few towns that has survived from that early era.


There are two waterfront areas, both along the Choptank: Sailwinds Park, home of the Visitor Center next to Route 50, and Long Wharf Park where the city marina is located.

Beach area at Cambridge Visitor Center
Beach area at Cambridge Visitor Center. It’s closed to swimming, but the next closest beach is Ocean City.

Sailwinds Park actually has two sections, split in half by Dorchester General Hospital, which is also on the waterfront. There’s the Visitor Center section by the Highway 50 bridge, and the Governor’s Hall section (200 Byrne Street) with the concert/convention hall.

The Dorchester County Visitor Center (2 Rose Hill Place, Cambridge, MD 21613) is where you want to head. It’s known for its 100-foot white sail covering. The center is open 8:30a-5p and has staff to answer questions. Inside, there’s an exhibit explaining the history of the area and it has all the standard tourist brochures. The balcony view of the water is worth a look-see.

Cambridge Visitor Center
Visitor Center at Sailwinds Park in Cambridge.
Cambridge Visitor Center
View of Choptank River from the Cambridge Visitor Center

The waterfront walk is nearly as pretty as the Hyatt waterfront (see below); that’s only because it’s slightly less manicured. But the center has a large public parking area and public restrooms. There’s a mile-long board walk along the water front that’s also part of the town’s bike path. It loops under highway 50 to the half-mile long fishing pier.

You’ll find  a small horseshoe-shaped beach at the Visitor Center, but signs are posted prohibiting swimming because it’s “under construction” and apparently has been for years. Locals have been known to pull out a beach towel and dip into the water.

Beach area at Cambridge Visitor Center at Sailwinds Park
Beach area at Cambridge Visitor Center at Sailwinds Park

While you can see the distinctive Visitor Center from Route 50 near the Choptank River bridge, there’s no direct road to get there from 50. Follow the signs for the visitors center and they’ll direct you around the streets easily enough. Sailwinds Park is about a 15-20 minute walk to the downtown section, but it’s not a particularly scenic walk. You’re better off using a car or bicycle to go there.

The other waterfront is Long Wharf Park with Cambridge Municipal Yacht Basin (also know as the city marina). Downtown Cambridge is about a 10-minute walk from here. High Street, between the two, is a great stroll along an oak-shaded, brick street with big antebellum and Victorian homes. There’s large public parking lots in both downtown and the marina, so you can drive to both but consider parking in one location and walking to the other.

The city marina’s office is the Choptank River Lighthouse (705 Leonard Ln, Cambridge, MD 21613), a replica of six-sided, screw-pile lighthouse. Visitors are welcome because it also doubles as a museum. There’s no fee, but they do have a donation jar. It has a few exhibits explaining the history of the original lighthouse and the area’s maritime history. Walk upstairs for a view out of the top windows, but you can also walk around the house’s circular outdoor balcony on the main level.

The lighthouse is normally open to the public for self-guided tours daily from 9a-6p, from May through October. Off-season visitors can see the lighthouse by appointment by calling 410-463-2653.


High & Commerce Streets

High Street is about two blocks of large antebellum and Victorian homes along a brick-paved street lined with large mature trees between the marina and downtown Cambridge. Many homes are beautifully restored. Others are undergoing restoration. There are a number of tours along High Street and historic Cambridge available by costumed guides, including a Civil War tour, heritage museums and gardens, and even a ghost walk.


Just off High Street, there’s a side road called Commerce Street. It doesn’t look like much more than an alley, but it leads to a couple of worth-visiting nuggets: the Clayton Seafood Company, the skipjack “The Nathan of Dorchester” and one of the town’s two waterfront restaurants.


The J.M Clayton Seafood Company (108 Commerce Street, Cambridge, MD, 21613) is one of the nearly 20 remaining Maryland blue crab wholesalers on the Chesapeake Bay, and the only one in Cambridge. For five generations (since 1890), the company has processed seafood purchased from watermen’s boats that line-up at the company docks every weekday afternoon.

J.M. Clayton Seafood Company, Cambridge, Maryland
J.M. Clayton Seafood Company processing plant in Cambridge

They sell crabmeat during the spring and summer and oysters in the fall and winter. Their products go to restaurants and seafood markets throughout the country.

There’s no store-front, but if you walk in and talk to the person at the office window, they’ll sell you pints of cooked crabmeat that are processed and picked in the plant.

They also give tours, but you should call in advance to see if someone is available. They walk you through the history of crabbing, and if you’re there during the work week, you’ll see employees process the boiling crabs in huge vats, while nearby, rows of “pickers” sit at stainless steel tables stripping the meat from the crabs the way it’s been done for generations. Here’s a fun video about the company:


The Nathan of Dorchester skipjack is a reproduction of the type of boats watermen used for generations on the Chesapeake Bay. They’re the state boat of Maryland; basically, they’re a fishing boat that runs on sail-power. The Nathan was built to be an oyster dredge but actually does tours on the Choptank River now, occasionally scooping oysters from the bottom of the Bay to show tourists how it’s done.

Snappers Waterfront Cafe, Cambridge, MD
Snapper’s Waterfront Cafe & tiki bar in Cambridge, MD. Boats can tie up at the pier. “Lady Katie” skipjack is in the front.

The skipjack has public sails usually on Saturdays and Sundays during boating season, but check the website’s schedule on times and dates. Reservations are recommended, but if there’s room they’ll also take walk-on passengers. Nathan picks up for public sails at Long Wharf at the end of High Street, May through October, but when not sailing you’ll find her docked in front of Snappers Waterfront Cafe on Commerce Street.

Snappers Waterfront Cafe (112 Commerce Street, Cambridge, MD, 21613) is one of two waterfront restaurants in Cambridge. They have a deck for outdoor seating by the water and a tiki bar in a sandy area that’s popular with the boaters who pull up at Snappers’ dock. There’s no docking fee.

Snappers is known for their crab cakes and Jamaican food. The owner and chef have a fondness for Jamaica and travel there frequently for ingredients and recipes.  There’s often live music on the weekends. The tiki bar is the summer home to a couple friendly, fat ducks who walk about the sand and don’t mind approaching you for snacks. One duck has been coming back to Snappers for five years.

Snappers Waterfront Cafe, Cambridge, MD
Entrance to Snappers Waterfront Cafe in Cambridge, MD. There’s waterfront seating on the other side.

Portside Seafood Restaurant (201 Trenton Street, Cambridge, MD, 21613) was originally an oyster house. Now it’s a family owned and operated restaurant specializing in local Chesapeake Bay seafood. Very casual. They have outside, waterfront dining upstairs and downstairs. This is the restaurant locals consistently mention when asked where to eat in Cambridge.

Portside restaurant, Cambridge, MD
Portside, one of two waterfront restaurants in Cambridge, MD. They specialize in nearly everything crab related.


Downtown Cambridge

Downtown Cambridge is actually “L” shaped. The short section is High Street, while the long sections is several blocks of storefronts on Race Street. The short section includes the historic courthouse and Christ Church, as well as several interesting stores and restaurants.

The historic Dorchester County Courthouse (206 High St., Cambridge, MD) was built in 1853 by a Maryland architect to look like an Italian villa and enlarged in 1931 with Georgian Revival decorative detailing added. The low-lying open lawn to the side is known as Spring Valley and has a cast iron fountain.

Dorchester County Courthouse, Cambridge, Maryland
Dorchester County Courthouse in Cambridge. Slave auctions were held on this front lawn.

Slaves used to be auctioned off at the front of the courthouse and Underground Railroad agents were sentenced there. It’s now on the National Register of Historic Places and was named by the National Park Services in 2005 as an official site of the Underground Railroad Network to Freedom.

Off to the side of the count house is a former “lawyers row.” It’s a short block of tiny historic houses that once served as lawyers offices so they’d have quick access to the county seat.

Across the street is Christ Church built in 1883. The Great Choptank Parish was actually established in 1692 in the colony of Maryland on behalf of King William and Queen Mary. The current building is the third of what is now Christ Episcopal Church. Next to it, enclosed by a beautiful brick wall and black iron fence is the old cemetery believed to date back to 1692.

Christ Church, Cambridge, Maryland
Christ Church in Cambridge

According to the church history, four Maryland governors are buried there: Charles Goldsborough, Henry Lloyd, Phillips Lee Goldsborough and Emerson C. Harrington. You’ll find a monument in the cemetery for Governor John Henry, who was a member of this parish. He was actually buried at his home “Weston” on the Nanticoke River, but erosion washed the grave away so they gave him a monument in Cambridge.

Christ Church, Cambridge
Christ Church cemetery in Cambridge, dating back to the colonial times & the Revolutionary War

Many colonial politicians are buried behind the brick walls as well as Revolutionary War patriots and veterans from the Civil War, the War of 1812, the Mexican War, the Spanish American War, Korea, World Wars I and II and Vietnam. “Christ Church is especially proud of the Revolutionary War patriots,” according a church historian. The oldest gravestones are near the High Street entrance.

On the next block down is a row of old store-fronts, including the former Nathans Furniture store building, now LivAgain (317 High Street, Cambridge, MD 21613), a consignment shop/antique store/art gallery all in a meticulously restored 1892 building. You can still see the furniture store sign on the outside of the building. It’s an interesting place to stop in.

The owners also have a moving company, so you’ll find some large, high-end pieces owned by retirees moving to the area who want to downsize. That’s on the first floor. The second floor is the art gallery, specializing in African American art.

At the corner of High Street and Locust Street, is the Richardson Maritime Museum (401 High Street, Cambridge, MD 21613). It’s often mistaken for a bank, which it was before becoming a museum. It’s named for Jim Richardson, a local boat builder who died in 1991, and boating is its focus. The exhibits feature boat replicas built by local modelers.

Richardson Maritime Museum, Cambridge, MD
Richardson Maritime Museum, featuring the traditional wooden sailing vessels of the Chesapeake Bay.

You’ll also find a collection of boatbuilders’ tools, watermen’s artifacts and photos from the 1930s of Cambridge Creek, then filled with bugeyes, buyboats, skipjacks and schooners. Don’t know what those are? Check out the boat models in the museum. It’s only open Wednesday, Saturday and Sunday. Check the website for times. They ask for a $3 donation.

Across from the maritime museum is the main drag, Poplar Street. This is where you’ll find several blocks of old-timey downtown buildings full of shopping and restaurants. If you’re a shopper or like to search for antiques, you can spend several hours strolling around main street. Cambridge Main Street keeps an updated list of the stores.

Cambridge Antique shop
Cambridge has turned several former industrial buildings into antique shops.

Some of the places locals recommend:

  • Bistro Poplar (535 Poplar Street), described as a shabby little French restaurant restaurant specializing in Eastern Shore produce and meats. Everyone asked about where to go mentioned Bistro Poplar first or second.
  • High Spot Gastropub (305 High Street), a casual pub with sidewalk seating. It was voted Best Happy Hour and Best Craft Brew Selection by “What’s Up” magazine. Locals recommend it as one of the “newer places.”
  • Jimmie & Sooks Raw Bar & Grill (527 Poplar Street), known for its cream of crab soup. The restaurant’s owner comes from a long line of Dorchester watermen. They specialize in local ‘comfort food’, from mussels to meatloaf.
  • Rar Brewing (504 Poplar Street), another of the “newer” places, having opened in 2013. They brew craft beer on the premises. Their beer is rated 4.07 out of 5 by, and the place gets a score of 96 out of 100. In the warm months, the large front window open to the street.
RAR Brewing
Looking through the front window of RAR Brewing, offering live music on the weekends

These are the bigger places. There are a number of smaller restaurants along downtown Cambridge.

One thing to note when shopping in Cambridge, many of the older merchants perfer cash or check and will charge extra for using a debt or charge card.

Harriet Tubman

Harriet Tubman, known as the ‘conductor’ of the Underground Railroad, was born in Dorchester County in 1822. She was a slave who ran away and returned 13 times to help about 70 family and friends escape. She was also a spy during the Civil War.

The Harriet Tubman Museum (424 Race St., Cambridge, MD 21613) is located in the middle of downtown Cambridge. It’s a small museum that tells her life story and is tucked away in a former shop.

Harriet Tubman museum, Cambridge, MD
Harriet Tubman museum

The museum is part of a self-guided driving tour with more than 30 sites dealing with the Underground Railroad. You can get a map and guide at the Visitors Center, or download it off the Harriet Tubman Underground Railroad Byway website. The museum is open Tuesday through Saturday 12p-3p (4p on Sat.).

Just off Route 50 is the Harriet Tubman Memorial Garden (Route 50 & Washington Street/Route 343, Cambridge, MD 21613). It features a number of murals of Harriet Tubman painted by Charles Ross, a Tubman relative.

Various stores in Cambridge feature works featuring Harriet Tubman by various artists, as well as African American artworks.


Just Outside City Center

Portside restaurant, Cambridge, MD
Portside, one of two waterfront restaurants in Cambridge, MD. They specialize in nearly everything crab related.

To get to downtown Cambridge, you cross a drawbridge over Cambridge Creek. Tucked next to the bridge, and easy to miss, is Portside Restaurant (201 Trenton Street), the other waterfront restaurant in Cambridge. It’s a popular, divvy little place known for crab dip, crab cakes, crab balls and crab soups. It’s a local’s favorite. There’s seating overlooking the water and the drawbridge. You can come by car or boat.

The maritime museum is connected to the Ruark Boatworks (Maryland Avenue & Hayward Street; Cambridge, MD 21613), which you pass on the way to downtown Cambridge. The plan is to eventually turn the large brick facility into a maritime heritage center. Currently, the facility is used to restore old boats and build new ones using the old methods. The boat works is open Mondays, Wednesdays, Fridays and Saturdays, but you may find it closed on Saturday if a docent isn’t available.

Antiques CambridgeAt the end of Dorchester Avenue, you’ll find old brick factories and warehouses. They’ve been assorted antique shops over the years, but Bay Country Antiques (415 Dorchester Avenue) has been around since 1980 and it’s huge. They specialize in high-end furniture and large antiques, but also have custom-made farm tables and just fun stuff.

Route 50

Route 50 is lined with many of the modern stores, strip malls, and chain restaurants found in any larger town. But there are a couple places to mention that have been there since before the chains and are local favorites.

Ocean Odyssey, Cambridge, MD
Ocean Odyssey, a long-time family owned restaurant featuring steamed crabs & local fish

Ocean Odyssey (316 Sunburst Highway, the local name for Route 50) is a family seafood restaurant that started as a crab factory in 1947. They only serve Maryland crab and the oysters are typically Choptank Sweets. It’s an old-timey ‘Route 50’ building and easy to overlook, but this restaurant has been featured on national foodie shows.

The menu is not typical of a fish place. It simply lists “fish” and you pick from what’s available that day. You’ll also find local bison burgers. They’ve recently added regional craft beers.

Bay Country Bakery, Cambridge, MD
Bay Country Bakery specializing in donuts, but also serving sandwiches

Kool Ice & Seafood (110 Washington Street, just off Route 50) is a seafood retail shop that buys from local watermen. They also sell bulk ice. You’ll find Chesapeake Bay fish of all types, oysters, clams and hard or soft crabs.

Bay Country Bakery (2951 Ocean Gateway) has been a must stop for many beach-bound travelers on Route 50. They have sandwiches, but are best known for their cake donuts and huge yeast (‘raised’) donuts, as well as pretzels.


Hyatt Regency Chesapeake

Hyatt Regency Chesapeake BayCambridge is probably best known these days as the home of the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina (100 Heron Blvd. at Route 50, Cambridge, MD 21613). It’s a 400 acre resort on the banks of the Choptank River. The groomed lawns and walkways along the river are beautiful, especially at night. It has indoor and outdoor bars with seating overlooking the waterfront. However, it’s mainly for hotel guests and while you can walk through, the non-guest parking is small and distant. This is a prime spot for weddings and conferences. It can be very busy.

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