Cambridge is one of the oldest colonial cities in the nation, founded in1684, but it’s no Annapolis or Chestertown with a lot of Colonial buildings. What makes Cambridge stand out is its retro-cool downtown and the outdoor sporting vibe.

It’s in the center of the Eastern Shore’s boating, cycling, hunting, and fishing region.

The Cambridge business district is undergoing gentrification and starting to boom with a mix of unique boutiques, art galleries, and restaurants, anchored by the regionally famous RAR Brewery.

Cambridge also has a beautiful waterfront on the Choptank River.

The two are connected by Cambridge Creek, which flows into the Choptank. Downtown is a few blocks from the river. Businesses evolved around the creek, which is now more like a canal.

Between the river and business district, you’ll find historic homes, traditional Chesapeake Bay seafood restaurants, and a Blue Crab packing house that’s still in operation.

Cambridge is also the gateway to the Blackwater Wildlife Refuge where former slave Harriet Tubman operated her portion of the Underground Railroad.

Downtown Cambridge

Downtown Cambridge has undergone a major revitalization in the past few years and it continued despite the 2020 pandemic.

The Cambridge city center is “L” shaped. The long side is a squiggle combination of Poplar and Race streets. The short section is High Street which leads to the Choptank River through a Colonial neighborhood.

Each section has a different vibe.

Poplar and Race Streets

Poplar Street is where the RAR Brewery is located and this section has evolved into the party section of downtown.

RAR Brewing (504 Poplar Street) is in an 80-year-old former pool hall and bowling alley. They rehabbed the building and moved in the summer of 2013.

The brewery’s growing popularity has been a boost for the downtown entrepreneurial spirit.

Boutiques, art shops, and antique stores continue down Race Street. This section of Race Street was listed as an Endangered Maryland site in 2014. It’s now a thriving fine dining area.

Buildings here continue to be rehabbed and people are coming in to stay for the weekend or summer due to the lively downtown and continuous festivals.

The Harriet Tubman Museum and Educational Center (424 Race Street, Cambridge, MD) is down the street in a small historic house in the middle of the block.

Harriet Tubman Museum in Cambridge

Harriet Tubman was an escaped slave who returned to the South 19 times to rescue more than 70 other slaves (some say she rescued closer to 300 slaves), traveling through the Dorchester County marshes along the Underground Railroad.

This is a different museum from the large Underground Railroad Museum operated by the National Park Service in the Blackwater Wildlife Refuge.

High Street

The Cambridge city center is “L” shaped. The oldest section is High Street, leading to the river.

This is an easy 10-minute walk to the waterfront.

At the business-district end is the Richardson Maritime Museum (400 High Street) commemorating Cambridge’s 300-year boat-building history. It has models of the many different types of waterman boats that operated on the Choptank River and the Chesapeake Bay over generations.

Richardson Maritime Museum, Cambridge, MD
Richardson Maritime Museum

You’ll find a collection of boatbuilders’ tools, watermen’s artifacts, and photos from the 1930s of Cambridge Creek filled with bugeyes, buyboats, skipjack, and schooners. Don’t know what those are? Check out the boat models in the museum.

Call the museum or click on the Richardson Maritime Museum Facebook page to find out when it’s open. They’ll ask for a small donation.

Farther down High Street you’ll find the historic Dorchester County Courthouse (206 High Street), built in 1853 by a Maryland architect to look like an Italian villa and enlarged in 1931 with Georgian Revival decorative detailing added.

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 courthouse 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.

Lawyers Row in Cambridge, Maryland
Cambridge’s Lawyers Row

Across the street is Christ Episcopal Church (215 High Street, Cambridge, MD) built in 1883. The Great Choptank Parish was 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 a 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 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

Closer to the water, it’s 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 several 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.

Commerce Street (a ‘Don’t Miss’)

Just off High Street is a side road called Commerce Street. It doesn’t look like much more than an alley, but it leads to 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.

J.M. Clayton Seafood Company processing plant 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.

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 crabmeat that are 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 workweek, 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:

Down the road a bit is Snappers Waterfront Cafe (112 Commerce Street, Cambridge, MD), 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 Waterfront Cafe in Cambridge, Maryland
Snapper’s Waterfront Cafe & tiki bar in Cambridge, MD. Boats can tie up at the pier. “Lady Katie” skipjack is in the front.

The Nathan of Dorchester skipjack is a reproduction of the type of boat watermen used for generations on the Chesapeake Bay.

The Nathan was built to be an oyster dredge but does tours on the Choptank River now, occasionally scooping oysters from the bottom of the Bay to show tourists how it’s done.

Nathan of Dorchester skipjack out of Cambridge, Maryland
Photo courtesy

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 the room they’ll also take walk-on passengers.

Once a year, Chesapeake Bay skipjacks race. You can watch them from Cambridge’s Long Wharf.

Harriet Tubman

Harriet Tubman, the best known of the Underground Railroad’s conductors, was born in Dorchester County in 1822. 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.

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.

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

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

The Harriet Tubman Underground Railroad National Historical Park is about 10 miles away in the Blackwater Wildlife Refuge. This is a federal historical site with several buildings providing a look at Harriet Tubman’s life and the era in which she lived.

It’s located in a beautiful marsh and a great cycling area.

Cambridge Waterfront

Sailwinds Park in Cambridge, MD

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.

Cambridge Sailwinds Park

Sailwinds Park has two sections, split in half by Dorchester General Hospital, which is also on the waterfront.

The Dorchester County Visitor Center (2 Rose Hill Place) 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.

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 boardwalk along the waterfront 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 has been for years.

Locals have been known to pull out a beach towel and dip it into the water.

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 known as the city marina).

Long Wharf Park in Cambridge

The city marina’s office is the Choptank River Lighthouse (705 Leonard Ln, Cambridge, MD), a replica of a 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.

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 are 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.

What Else to See and Do in Cambridge?

When you drive to downtown Cambridge, you cross a drawbridge over Cambridge Creek. Tucked next to the bridge, and easy to miss, is Portside Seafood Restaurant (201 Trenton Street), the other longtime waterfront restaurant in downtown Cambridge.

It’s a popular little place known for the crab dip, crab cakes, crab balls, and crab soups. It’s a local 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), 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.

At 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.

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

They specialize in high-end furniture and large antiques, but also have custom-made farm tables and just fun stuff.

NOTE: When shopping in Cambridge, many of the older merchants prefer cash or check and will charge extra for using a debt or charge card.

Hyatt Regency Chesapeake

Hyatt Regency Chesapeake Bay

Cambridge 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).

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 and can be very busy.

Blackwater National Wildlife Refuge

Blackwater Wildlife Refuge

Nearby Blackwater National Wildlife Refuge is more than 20,000 acres of Maryland marshland. With five miles of hiking and 17 miles of paddling.

It also has a beautiful 3.6-mile wildlife drive. You can turn it into a 7-mile cycling loop, or a 20-mile flat bicycle ride (or more) by adding county roads.

Blackwater Wildlife Refuge
Blackwater National Wildlife Refuge Drive

Be aware if you’re cycling, the roads don’t have shoulders.

There’s also a visitors center, but check the website to see when it’s open. The drive and trails are open every day, dawn to dusk. Some water trails close in the fall and winter.

Where to Stay in Cambridge

Cambridge has plenty of motels along Route 50 and there are historic B&Bs in the city.

Dorchester County’s tourism office has an updated list of places to stay in the area.

Cambridge Annual Events

Cambridge has many annual events, a lot of them involving the Choptank River. Some of the most popular include dragon boat races in the spring and skipjack races in the summer. There are several organized cycling rides through Blackwater National Refuge.

As the area recovers from the coronavirus pandemic, those events will be scheduled again. Dorchester County is staying updated on Cambridge area events.