The quaint, bustling Eastern Shore town of St. Michael’s has a lot to offer and is the perfect weekend getaway for those seeking some R&R. Located off the Eastern Bay and Miles River, St. Michaels dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. The town still reflects its colonial past with its many preserved historic homes dating from the late 1700s and 1800s. Whether you’re looking for historical charm or nautical adventure, St. Michael’s is the place to be. Here’s our suggested day itinerary, whether you plan to stay for either the day or an extended weekend trip in one of the many charming inns.

What To Do

1. Explore the historic downtown’s Talbot Road. Wander into whichever stores look interesting for fun oddities, apparel, and art, then get a coffee and pastry at the Blue Crab tucked just behind the main street to keep you fueled.

2. Stroll around historic neighborhoods. We swear, simply strolling around the picturesque town is an art form here – especially when you have to also pay attention to the uneven brick sidewalks. Once you’re finished meandering Talbot Road, pop down the side streets to admire the historic and beautiful homes. If you’re interested in learning more about the building’s histories, the St. Michaels Museum put together this helpful guide.

3. Walk down Cherry Street and cross Honeymoon Bridge towards the pier. The bridge has connected the foot of Cherry Street to Navy Point for pedestrians since the late 19^th century when the first summer guest cottages opened along the Navy Point waterfront. From the small foot bridge, you’ll spot the Museum’s Hooper Strait Lighthouse straight ahead. The bridge is a worthwhile stop for a quick photo.

4. The Chesapeake Bay Maritime Museum is home to a collection of Chesapeake Bay artifacts, exhibits, and vessels. The 18-acre interactive museum is located on the water at the site of former seafood packing houses, docks, and work boats, plus the Hooper Strait Lighthouse dating from 1879. Come in the late afternoon for fewer crowds and a gorgeous view of sunset over the bay.

5. Muskrat Park is a cute little park off the water and close to the main street shops. Sit and enjoy the view.

6. Get out on the water and take a boat ride or kayak to enjoy the water and get a different perspective of the town.

7. Christ Church Episcopal and Union Methodist Church are both unique and historic structures. Plus, you may spot some of the local families’ headstones at the Christ Church graveyard – pay attention, and you’ll notice these names come up over and over again.

8.Sample local beer and wine at Eastern Shore Brewing and St. Michaels Winery. Located right in town and across the street from one another, you hardly have to move to get a taste of these popular local watering holes.

Where To Eat

The Blue Crab Coffee Co. – a sweet local gem tucked right off the main street. Erected in 1883 and former home of the Freedom’s Friend Lodge of Odd Fellows, the building is now home to a coffee shop serving up delicious coffee, espresso and tea drinks plus a café style menu with quality ingredients. Rest your feet and sip coffee while playing board games located in the back.

Foxy’s Harbor Grill – slightly elevated bar style food inspired by the mid-Atlantic with a great view of the bay. Watch boats pull up and dock as you enjoy the fresh breeze coming off the water. Try the crab pretzel and crab sandwich, and don’t forget to cool down with a tasty cocktail. Dog friendly.

Ava’z Pizzeria & Wine Bar – Spot with fantastic pizza (we do not claim this lightly) with a solid beer list. If there’s a wait, we promise it will be worth it. Check out their creative beer tap fountain on the twinkly light back patio.

Bistro St. Michaels – New American restaurant with a fresh menu sure to satisfy everyone’s taste buds.

Limoncello Restaurant & Wine Bar – Charming bistro serving up very good Italian fare with wonderful service. Ideal for a special date-night spot.

The Inn at Perry Cabin – The restaurant at this tucked away resort is impeccable. Enjoy the outdoor patio tucked into beautiful landscaping under shaded awnings. Plus the entire grounds are absolutely stunning.

Looking for a place to stay? We’ve personally stayed at Wade’s Point Inn On the Bay and couldn’t recommend it highly enough. Think beautifully decorated rooms in a historic structure (our room even had a claw foot tub) with picturesque views of the bay and super friendly staff. Check out photos from our stay below!