24 Hours in Cambridge

Twenty-four hours is just long enough to explore the vibrant contemporary Cambridge.

The Eastern Shore of Maryland is a place where change comes slowly, if at all. Which makes the changes experienced by Cambridge—from colonial port to 19th century oyster- and tomato-packing juggernaut to the post-1950s economic slump and subsequent race rioting—that much more remarkable. But scrappy Cambridge, situated on a wide bend in the Choptank River, isn’t done transforming yet. The last ten years have brought a fresh infusion of creative restaurants, a craft brewery with a cult status, and an eclectic mix of art galleries and shops to its lovely, quintessentially Chesapeake downtown. Twenty-four hours is just long enough to explore the vibrant contemporary Cambridge—and head home with a blue-crab food baby, to boot.

Irreverent Brews
A cold beer or two at RAR Brewery (504–506 Poplar St., 443-225-5664; is a great way to become acquainted with Cambridge’s new, hip Chesapeake vibe. This taproom/brewery combo has a reputation for the unexpected—its experimental and regionally minded beers have been inspired by Smith Island Cake (10 Layers), blue crabs (Bottom Feeder), and local rivers (Chopdank, Nanticoke Nectar), to name a few. Music spills from the lively, lofty downtown brewery where lines can wrap around the corner on new-beer release days, and an afternoon whiled away with a cold draft or two of their latest concoction is an excellent way to sample a little local flavor.

Picker’s Paradise
Rekindle your love for the bright, cheerful kitsch of Chesapeake oyster cans in Bay Country Antiques (415 Dorchester Ave., 410-228-5296;, where dozens of eye-popping examples of early marketing are waiting for a spot on your living room wall. Set in a massive warehouse in Cambridge’s old industrial district, you’ll ramble through room after room of Eastern Shore nostalgia—cases of oyster plates, old filling station signs, oyster baskets, fishing poles and regionally carved decoys that are as much local museum as merchandise. 

Comfort Food with a Twist
After a long afternoon walking though Cambridge’s 19th-century streets, take yourself and your rumbling belly over to the High Spot (305 High St., 410-228-7420; where Chef Patrick Fanning works magic on true-blue regional ingredients. Housed in a beautifully restored turn-of-the-century building, the menu proffers local, sustainable, flavorful staples. The fried green tomatoes topped with local crab and pimento cheese are life-giving—fresh, bright and toothy with a satisfyingly crispy crust—but the real star is the duck-fat burger. Made of local beef and fried in duck fat, then topped with smoked gouda, mushrooms and a gooey fried egg, this monster will make you beg for mercy in the best way possible. Wash it all down with a cold brew and enjoy your Elvis-style, fried-food afterglow.

Zeus Juice
Resist the temptation to head to bed early and stroll over to the Wine Bar (414 Race St., 410-253-9248) for a glass of wine served from its bank of wine taps or a tot of small-batch bourbon to wind down the day. There’s a well-curated selection of charcuterie and cheeses for those looking for something savory, but sugar fiends will find plenty of fodder in the dessert menu (Smith Island Cake, I’m looking at you!). 

Sunrise Snaps
Work up an appetite—and bring your camera—as you head down to the Cambridge Creek waterfront, where you’ll get a prime view of the workboats and watermen servicing harbor-front restaurants and the oldest operational crab-packing house in the U.S., the J.M. Clayton Seafood Company. The best vantage point is overlooking the harbor from the grassy lawn of the Ruark Boatworks and Brannock Education Center (103 Hayward St., 410-221-1871). Although many of the vessels are now recreational, there are still plenty of working deadrises and skipjacks that call Cambridge Creek home. You haven’t felt the heartbeat of the Chesapeake until you’ve seen one coming in at sunrise, laden with bushel baskets—and it makes a pretty picture.

Sunny Side Up off the Beaten Path
Just outside of town is locally beloved Cindy’s East Side Kitchen (3127 Aireys Rd., 410-228-3830), where the diner food is hot, tasty and filling. Cindy’s is a no-frills, no-fads joint where it could be 1965, 1985 or 2017, and everybody likes it just the way it is. That said, it’s easy to obey the “no sniveling” sign on the wall of this 1940’s Cambridge institution because you’ll be too busy shoveling airy grits and perfectly browned scrapple into your eager mouth. Local watermen and Ocean-City-bound-families sit peacefully alongside each other, humbled by their groaning plates of honest, delicious grub. A slice of pie to send you on your way and the hand-totaled bill just might hit $12. 

Real Talk on Race Street
Although the Harriet Tubman Underground Railroad National Historical Park in South Dorchester County is getting all the attention, Cambridge had a Harriet Tubman Museum and Education Center (424 Race St., 410-228-7977; long before the feds got involved. The museum volunteers and displays are informative, the real experience is a conversation with board member, local and national treasure Bill Jarmon. Call ahead to schedule a time to chat frankly with Jarmon about Tubman and her legacy, black history in Cambridge, and what it was like to live through the riots of 1967. Jarmon, a dyed-in-the-wool “from here” is remarkably candid and thoughtful as he shares his memories of Cambridge’s turn from packing house prosperity to down-and-out and back again. If you want to keep the conversation flowing, ask Jarmon for his fascinating walking tour of downtown Cambridge. You’ll walk away with a deeper, more nuanced understanding of the Eastern Shore’s complex Southern culture.

A Little Slice of Heaven
Pizza as good as Stoked’s (413 Muir St., 443-477-6040; should come with a waiver for temporary insanity. Be brave and try the Clam and Bacon pizza—the meaty sweetness of the bacon is phenomenal paired with the ocean tang of the clams. More conservative diners can’t go wrong with a classic Margherita pie or the hefty, perfectly golden crabcakes. For a lighter meal, demolish a mess of Stoked’s 17 flavors of wings and channel your inner velociraptor. There’s a great selection of craft sodas, if that’s your speed, and for folks who sense it’s five o’ clock somewhere, the extensive, creative cocktail menu will have the perfect tipple to wet your whistle. 

If You Go
For cruisers, the Cambridge Yacht Club (410-228-2141;, the Cambridge Municipal Yacht Basin (410-228-4031; and the Hyatt Regency (410-901-1234; all offer transient slips. Located on the waterfront, the slips are an easy stroll to the downtown area past the stately 18th and 19th century homes of Cambridge’s captains of industry.

People who drive over can bunk for the night at one of Cambridge’s exceedingly charming B&B’s. The Mill Street Inn (410-901-9144; is a tastefully restored, comfortable Victorian in the historic district with a warm atmosphere and some well-outfitted guest rooms.