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Iconic destinations dot the East Coast and lure hundreds of thousands of visitors to its shores every year. Places like Cape Cod, Nantucket, and Martha’s Vineyard are synonymous with summer vacation. While they’re beautiful places to visit, no doubt, their popularity also means they tend to get quite crowded. We’ve found another East Coast destination that’s still wonderfully under-the-radar and equally charming.

The historic town of St. Michaels, Maryland sits right along the Chesapeake Bay (about two hours east of Washington DC) in the heart blue crab country. It’s history can be tracked back to the 1600s when it served as trading post for tobacco farmers and trappers. Today, St. Michaels is home to less than 2,000 people and a favorite vacation destination of in-the-know East Coasters. The town, easily enjoyed over a long weekend, is chock-full of amazing seafood favorites and oozes charm at every turn. Ice cream parlors and sidewalk cafés line the main street, and there are numerous shops to pick up a Chesapeake keepsake. Those are just some of the reasons we think St. Michaels is the most under-the-radar secret gem in Maryland…but read on for more and decide for yourself!

RELATED: 5 ways Baltimore is taking a bite out of DC’s food scene


1) Crazy amounts of crab


Crab Cake Benedict at Bistro St. Michaels | Photo by Compass + Twine

Food is one of the best ways to get to know a destination and based on the offerings here, St. Michaels could be called Crab Town, USA. Start your day at Bistro St. Michaels with an order of Crab Cake Benedict and one of their signature breakfast cocktails. Lunch is best enjoyed outside and we suggest you snag a seat at one of the picnic tables and dine al fresco at St. Michaels Crab & Steak House right in the marina. Order local, just caught oysters and a bucket of steamed crab for a perfect Maryland meal. At the waterfront restaurant Stars, enjoy a myriad of dishes full of juicy, freshly picked Blue Crab Meat. Captain Perry’s Crab Cakes are served with corn succotash, the perfect summer pairing!

2) Locally owned Main Street


Shops along South Talbot Street | Photo Credit:

You don’t have to wait until Small Business Saturday to delve into the local offerings here. In St. Michaels, you won’t find a single chain or big box store. From home goods and antiques, to clothing boutiques and pet stores, the people of St. Michaels have you covered. Stroll or bike along South Talbot Street, the main drag through town, and sample treats from the bakery or satisfy your sweet tooth at the neighborhood candy shop.

ALSO: With Orbitz Rewards, you’ll never be crabby!

3) Get out on the water


Sailboats in St. Michaels | Photo by Compass + Twine

You can’t come to St. Michaels and not see the town from the water. Enjoy an afternoon sail or indulge your outdoorsy side with a kayak or paddle board adventure. Almost all year long, you can enjoy an oyster or lobster tour where you’ll get a front row seat to see where your dinner comes from! If you don’t have sea legs, live vicariously through sailors at the St. Michael Maritime Museum.

4) Happy Hour, Maryland style


Beer flight at Eastern Shore Brewing | Photo by Compass + Twine

If you’re thirsty for some local flavors, pop into Eastern Shore Brewing (dog friendly!) and sample a flight of their beers. Play a round of foosball while sipping a brew or try your skill at the ring toss game (nearly impossible!). Next door, St. Michaels Winery offers year-round tasting in if beer ain’t your thing.

5) Plenty of places to stay


Charming historic home | Photo by Compass + Twine

The people of St. Michaels have made it easy on visitors. From B&B’s to cozy inns, this town has no shortage of places to rest your head. Stay right in town at the St. Michaels Inn and you’ll have no need for a car! One of the best parts about visiting St. Michaels is that  the town is completely walkable and the streets are lined with beautiful historic homes that you can easily spend an afternoon admiring. Many of the charming accommodations are in old homes as well, so you’ll get to experience some of the history of the town during your visit.

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Tagged: New England

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