Beach hat, shoes, and lavendar plant on white linens.

What Are the Best Road Trips to St. Michaels, MD?

The Chesapeake Bay is the heart of the Eastern Shore. St. Michaels hugs the bayside, yielding beautiful of sparkling waters and warm-hued sunsets. While most travelers spend a lot of their time here relaxing by the water, there’s also plenty to do in this small town! Taste fresh seafood like Maryland-steamed blue crab, visit a winery or brewery, as well as some iconic museums and historical sites. Explore the Eastern Shore on these road trips to St. Michaels, MD.

Top 3 Places to Take A Road Trip to St. Michaels, MD


St. Michaels is the perfect in-state road trip destination from Baltimore. Travel southwest down Route 50 for an hour and a half to reach your bayside oasis. On your way, you’ll pass over the Chesapeake Bay Bridge. This bridge spans over the blue waters of the bay and serves as the medium between the cities on the West and the rural towns of the East. Disconnect from the reality of everyday life and explore a simpler life in your own backyard. Even if it’s just for a weekend, you’ll be glad you did!


St. Michaels, Maryland, is also a great road trip option for those in the Keystone State. With 1.5 million residents, life in the big city can be overwhelming at times. Need a getaway? Look no further than the Eastern Shore. Our small town is just a little more than a two-hour drive from the big city and offers unique things to do that you won’t find back home.


Retreat 80 miles to the East to escape reality while also experiencing some of the comforts of home. Did you know that Washington D.C. residents drink the most wine per capita in the United States? If you’re from the big city and this figure applies to you, don’t worry. We’ve got you covered here. St. Michaels Winery for locals and visitors alike.

Enjoy a wine tasting while you’re here, then take a bottle back home to enjoy with friends! D.C.residents can even join the winery’s Grand Crew Wine Club to keep some bayside relaxation in their life even after returning home. Lyon Distilling Co. is another great spot for spirits lovers to try!

Stay on the Eastern Shore at Wades Point Inn

Arrive at our Chesapeake Bayside property for the most authentic Eastern Shore getaway. Our inn just a stone’s throw away from the best views of the bay. You can even see it from some of our comfortable guest rooms! We’re also near the popular Chesapeake Bay Maritime Museum as well as great restaurants that serve up delicious fresh seafood and local fare.

For optimal privacy, reserve a room in our Two-Story Farmhouse. This stand-alone building has an expansive lawn, water views, and four guest rooms. Take a long weekend with close family or a couple of friends on a road trip to St Michaels, MD, and book a stay in our farmhouse’s Holiday Room.

Exterior view of the Farmhouse at Wades Point Inn on the Bay.

this room has a double bed, single bed, daybed, private bathroom, and water views. Browse all of our waterfront lodging options and book your favorite today!