Day Trip to St. Michael’s on Maryland’s Eastern Shore

Enjoy these beautiful sunsets and sailing adventures on a day trip to St. Michaels on the Eastern Shore of Maryland

If your summer plans don’t already include a day trip to the charming town of St. Michael’s on Maryland’s Eastern Shore, it’s about time you planned one. Our Bed and Breakfast on Maryland’s Eastern Shore is the perfect place to escape this summer, especially if you need a bit of solitude and zen-like relaxation. We wouldn’t blame you if all you wanted to do while here is sit back with a good book and relax, but we’d be remiss not to mention all the great things to do on the Eastern Shore, including taking a day trip to the charming town of St. Michael’s.

St. Michael’s is a picturesque harbor town located approximately an hour south of our Rock Hall Bed and Breakfast. USA Today named it one of the top 10 coastal towns in America, so you can count on it being more than worth the drive to spend the day here. Once you’ve had this fill of St. Michael’s, the comfortable accommodations at our Eastern Shore Bed and Breakfast will be waiting for you. Book your room today!

Walking along the harbor in St. Michaels on Maryland's Eastern Shore

Day Trip to St. Michael’s, Maryland

Though there is more than enough to do in Rock Hall and the surrounding Chesapeake Bay, it’s sometimes fun to get out and explore. A day trip to St. Michael’s on Maryland’s Eastern Shore is a perfect choice! St. Michael’s is a charming town on Maryland’s Eastern Shore, filled with a delightful combination of bustling marinas, delicious restaurants, and one-of-a-kind boutiques. St. Michael’s is also home to the excellent Chesapeake Bay Maritime Museum, which is a great place to learn even more about the history and life on Maryland’s Eastern Shore.

Like many towns on Maryland’s Eastern Shore, St. Michael’s has a lengthy and fascinating history that dates back to the mid-1600s when it served as a trading post for area tobacco farmers and trappers. Today, there are plenty of wonderful things to do in St. Michael’s, centered around its historic square, St. Mary’s Square, and its bustling harbors. Here’s a roundup of eight of our favorite things to do in St. Michael’s on Maryland’s Eastern Shore:

  1. Get established in the town by taking a self-guided walking tour of St. Michael’s on Maryland’s Eastern Shore.
  2. Take historic narrated cruises through St. Michael’s Harbor, or charter a boat and enjoy a sailing excursion in The Chesapeake Bay. You can even combine wine tasting with a sailing adventure in St. Michael’s!
  3. Enjoy some unique shopping in downtown St. Michael’s, where you’ll find a diverse range of shops and art galleries to browse.
  4. Rent a kayak, SUP, or bike from Shore Pedal and Paddle, and enjoy a day exploring St. Michael’s on Maryland’s Eastern Shore, just as you would beautiful Rock Hall, MD.
  5. Visit the Chesapeake Bay Maritime Museum and learn all about the history of this unique part of the world.
  6. Sometimes, there’s nothing better than relaxing with a cold pint of locally crafted beer on a hot summer day. You’ll find some delicious craft brews at Eastern Shore Brewing in St. Michael’s.
  7. Plan to attend at least one of the fun festivals in St. Michael’s! The most popular ones include WineFest at St. Michaels in April, St. Michaels Brewfest in May, and the Wine & Food Festival and OysterFest in October.
  8. Don’t forget to eat plenty of crab, oysters, and other local delicacies – it’s part of everyday life here on Maryland’s Eastern Shore, and it’s no different at the best St. Michael’s restaurants.

One of the wonderful cottages at our Bed and Breakfast on Maryland's Eastern Shore near St. Michael's

The Best Place to Stay on Maryland’s Eastern Shore

Though spending a day in the charming town of St. Michael’s is a wonderful thing to add to your itinerary to Maryland’s Eastern Shore, there’s something other-worldly about staying on our 70 zen-like acres near Rock Hall, MD. Our Eastern Shore Bed and Breakfast is rated as one of the best places to stay, and it won’t take you long to see why for yourself.

Maryland’s Eastern Shore is an easy escape from crowded cities like Baltimore, Washington D.C., and Philadelphia – and no matter the time you visit, you’ll find this beautiful part of the world serves as the tranquil and refreshing paradise you’ve been looking for.

Our Bed and Breakfast on Maryland’s Eastern Shore offers so much more than a comfortable place to call home at the end of the day. Though our accommodations are exceedingly comfortable, you’ll find that staying here goes far beyond a simple place to sleep. The amenities included in your stay, attention to detail, and exceptional hospitality work in concert to set our Eastern Shore Bed and Breakfast apart from its competitors.

Moreover, we’ll prepare you a fresh and delicious breakfast each morning of your stay. It’s the perfect fuel for whatever adventure lies ahead, including a day trip to the quaint town of St. Michael’s. Though you aren’t very far away from bustling metropolises, you’ll feel like you’re on an entirely different plane. It’s one of the best parts about staying with us on Maryland’s Eastern Shore. Isn’t it time you booked your room at our luxury Bed and Breakfast?

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