Where to Eat and Drink in Dorchester County, Maryland

About an hour and 40 minutes from both Baltimore and Washington D.C., Dorchester County is located on Maryland’s Eastern Shore. It’s Maryland’s second largest county by land but second smallest by population. While it tends to be overshadowed by its louder and more popular Eastern Shore neighbor, Ocean City in Worcester County, Dorchester County shouldn’t be overlooked.

My mother and I recently spent a weekend there and we both fell in love with its quaint neighborhoods, rich history and relaxing feel.  However, Dorchester’s food and drink scene alone makes it worth checking out for a night’s stay on your way to or from other Eastern Shore locales, or a weekend getaway all on its own.  I can personally attest that you’ll enjoy every bite or sip at the places listed below.

Where to Eat


The High Spot

The High Spot (305 High St, Cambridge, MD 21613) is a popular gastropub, located right in the heart of downtown Cambridge.  Owned and operated by Chef Patrick Fanning, brunch here is an absolute must as they serve fresh, local foods.  For starters, I tried their amazing pumpkin, chocolate, and streusel pastries.  All of the breads and pastries served are made fresh daily at their sister restaurant, Black Water.

Next I sampled their chocolate french toast made using Israeli Babka bread and battered in cinnamon whiskey.  It was so delicious and fresh! And for an added pop, I tried the french toast with a little goat cheese.  I was happily stuffed by the time we finished.


The Wine Bar

Located in downtown Cambridge, The Wine Bar (414 Race St, Cambridge, MD 21613) opened its doors about 13 years ago.  They offer a vast selection of domestic and international wines, cheeses, charcuterie and sushi that you can either sit and enjoy or take home.

The Wine Bar also sells an array of chocolate treats from Asher’s Chocolate in Pennsylvania, as this is the owner’s hometown. The staff at The Wine Bar provided excellent guidance and recommendations about what to sample.  I am still obsessing over the Cotswold cheese that I tried and fell in love with here.


Jimmie & Sook’s Raw Bar & Grill

In the mood for seafood? Jimmie and Sook’s (527 Poplar St, Cambridge, MD 21613) is the place to go! Named for male crabs (Jimmies) and female crabs (Sooks), this was some of the freshest seafood I’ve ever had.  I am still licking my fingers over their delicious crab soup, rockfish and desserts (and so is my mom!).

Cream of Crab Soup
Walnut encrusted rockfish, cheddar grits and baked sweet potato
Crab stuffed rockfish with cheddar grits and steamed broccoli
Dessert Tray

I loved the atmosphere here.  Jimmie & Sook’s is a place to go for a nice, casual dinner with friends, family or significant other.  They also have a live band on Saturday nights starting at 10 p.m. if you want to keep the party going. And if you’re ever in Belize, visit the their sister restaurant, Wet Willie’s Dock.

Where to Drink


RAR Brewery

Started by two friends and Dorchester County natives in 2013, RAR Brewery (504 Poplar St, Cambridge, MD 21613) brews its own beers in house.  They converted an 80-year-old former pool hall and bowling alley into a brewery where they brew 10 barrels at a time.  While they’ve been on tap at some of your favorite Baltimore and D.C. restaurants for some time, RAR has recently began a canning operation so they’re now distributed at retail stores throughout Maryland and D.C.

I sampled each of the beers they currently offer and there’s something for both dark and light beer drinkers.  My favorite was ‘Big Lizz,’ the butternut squash seasonal ale, but each of the beers offered was distinctly different. RAR describes each of their beers perfectly, so it’ll be easy for you to decide what you want…that’s if you decide not to try them all, which I highly recommend!

This is by far one of the coolest places in Dorchester County.  RAR also serves finger foods (because you can’t drink on an empty stomach…duh) if you want to sit and watch a game or hang out with friends. On most Saturday nights, they have a live band for entertainment.  I can see RAR serving as the center of nightlife as Dorchester County continues expanding its tourism offerings.


Layton’s Chance Vineyard and Winery

Layton’s Chance Vineyard and Winery (4225 New Bridge Rd, Vienna, MD 21869) is a family owned and operated winery in Vienna, MD, about a 20 minute drive from Cambridge.  Their motto is “We work like crazy, so our guests can be lazy.”

During my visit, Layton’s Chance was hosting their annual Harvest Festival with many activities for the entire family.  There was wine tasting, pumpkin picking, grape stomping, a live DJ for dancing and vendors where you could buy various items such as jewelry and handmade soaps.

Before planting grapes in 2005, the family used the farm to run a successful grain operation.  In order to expand their business, the Layton family decided to start a vineyard and haven’t looked back since.  Layton’s Chance wines are currently sold in 150 retail outlets in Maryland and shipped to over 13 states.  Offering white, red and fruit wines in sixteen varieties, ‘Turbo Charged Joe’s Cool Red’ is their most popular and happened to be my favorite, at 18% alcohol.

Honorable Mentions

I didn’t get a chance to try these places, but I’ve only heard good things. Give them a try if you have time:

I was pleasantly surprised about how much I enjoyed exploring Dorchester County through their local foods and spirits.  I highly recommend spending a night or making a weekend out of seeing all that Dorchester County has to offer.

While this trip was hosted by Dorchester County Tourism, all opinions are my own.