How to Plan the Ultimate Day Trip to St. Michaels, MD

Are you looking for hidden gems along Maryland’s Eastern Shore? While there is plenty to see and do in historic Chestertown, many of our guests enjoy a day trip to St. Michaels, MD, during their stay. Filled with bustling marinas, fabulous restaurants, and one-of-a-kind boutiques, this charming waterfront town is well worth the visit. Here’s what you’ll discover when you go!

Things to Do in St. Michaels, MD

Whether exploring by land or sea, you’ll love every second of your visit to St. Michaels, MD. Once known as a hub for shipbuilding and oystering, this Eastern Shore of Maryland town is now a prime destination for boaters, outdoor enthusiasts, and history buffs alike. Spend a day exploring museums and historic sites, kayaking along beautiful creeks and rivers, or sipping through some of Maryland’s best wineries, breweries, and distilleries. The possibilities are endless!

For a day trip, we recommend adding the following activities to your itinerary:

1. Visit the Chesapeake Bay Maritime Museum

If there’s one thing you must do in St. Michaels, it’s visit the Chesapeake Bay Maritime Museum! This 18-acre interactive museum features an excellent collection of Chesapeake Bay artifacts, exhibitions, and a floating fleet of historic boats. Take a step back in time and learn about the history and culture of our gorgeous region. Climb to the top of the 1879 Hooper Strait Lighthouse and enjoy breathtaking harbor views. Or, hop aboard the museum’s 1920 Winnie Estelle boat and enjoy a scenic river cruise. One thing’s certain: you won’t run out of ways to explore at the Chesapeake Bay Maritime Museum!

Are you looking for even more history? Here’s another look at the unique Chesapeake Bay history.

2. Take a Boat Tour Along the Miles River

Speaking of boat tours, here are two other great river cruises to add to your list! Patriot Cruises offers some of the best historical, narrated cruises in St. Michaels. Enjoy the ride as your experienced guide tells you about the town’s history, which dates back to the American Revolution. Along the way, you’ll see 300-year-old Victorian mansions, beautiful scenery, and native wildlife. Keep an eye out for dolphins and osprey!

Sail Selina II also offers excellent Chesapeake Bay boat tours and sailing charters in St. Michaels, MD. This luxury sailing yacht can accommodate six guests, so it’s perfect for those looking for a more intimate experience.

3. Reconnect With Nature

St. Michaels is an outdoor enthusiast’s dream, from fishing and boating to sailing and kayaking. Would you like to spend a day on the water? Enjoy a relaxing paddle along San Domingo Creek, Oak Creek, Miles River, or Leadenham Creek. Are you planning to do some fishing while on vacation? Cast a line right into the Bay for catfish, largemouth bass, and rainbow trout.  If you’d like to get your adrenaline pumping, rent bikes and pedal along scenic Route 33 or impressive nature trails.

4. Dive Into History at St. Michaels Museum

Calling all history buffs! Located inside a 19th-century home, the St. Michaels Museum features regional exhibits and walking tours. Docent-led tours are held on Saturdays at 10 a.m. from May through October. However, you can also schedule a self-guided tour any day you please.

5. Sample Delicious Wine, Brews, and Spirits

When you’re ready to unwind, check out some of the breweries, wineries, and distilleries in St. Michaels. Lyon Distilling is a favorite spot for locals and visitors alike. This popular nano craft distillery is especially famous for its small-batch rum. Stop into the tasting room (it’s open seven days a week) and sample some of Maryland’s finest liquors!

Perhaps you’re in the mood for an ice-cold beer? Enjoy a tasting at Eastern Shore Brewing! The oldest brewery on the Eastern Shore of MD, it’s also one of the best. From amber ales and hoppy IPAs to dark and delicious porters, their award-winning brews will surely impress!

Wine lovers will want to make a stop at St. Michaels Winery. This local winery is open Thurs-Mon and has 20+ delicious wines. Dry-wine flights, sweet wine flights, and by-the-bottle options are available. No reservations are required, so feel free to drop in and try them all!

A group of friends enjoying an outdoor meal with white wine

Dining in St. Michaels, MD

Are you craving fresh Maryland blue crab? Or perhaps you’re in the mood for authentic Italian, Irish, or Southern cuisine? When it comes to restaurants while on your day trip to St. Michaels, the hardest decision you’ll have to make is which one to try first. From casual crab houses to romantic bistros and fine dining establishments, there are many fantastic places to drink and dine. Here are some of our top recommendations for a day trip:

1. Ava’s Pizzeria and Wine Bar

This cozy restaurant is one of the town’s most popular eateries for a reason. Stop into Ava’s for delicious Italian fare, wood-fired pizzas, and seafood fresh from the Bay.

2. The Crab Claw

Nothing compares to the taste of fresh Maryland blue crab! This local crab shack opened in 1965 and has served delicious seafood ever since. Open March through October, The Crab Claw is as seasonally fresh as it comes! Enjoy beautiful views of the Miles River while you dine.

3. Limoncello Italian Restaurant and Wine Bar

You must try Limoncello’s if you’re looking for an authentic Italian dining experience. With entrees like Ravioli con Astice, Linguine con Vongole and Pappardelle allo Zafferano, each mouthwatering dish sounds better than the last! There is also an excellent selection of exclusive Italian wines and seasonal cocktails in a casual dining atmosphere reflecting the beauty of Southern Italy.

4. Bistro St. Michaels

Bistro St. Michaels is a favorite brunch and dinner spot with a romantic ambiance and delicious New American fare. The menu features an array of hors d’oeuvres, savory soups, salads, entrees, and wine. We highly recommend the Coq Au Vin and Lamb Ragout!

5. Justine’s Ice Cream Parlor

Certainly after lunch or dinner, you’ll want to stop into Justine’s Ice Cream Parlor for some of the best scoops along Maryland’s Eastern Shore. Choose from 42 premium flavors of hand-dipped ice cream, soft-serve ice cream, frozen yogurts, sorbet, and sherbets!

Three women in sunglasses and holding shopping bags while looking in a shop window

Shopping in St. Michaels, MD

On your day trip to St. Michaels you’ll also find fabulous shopping opportunities. Here, you’ll find unique antique stores, trendy boutiques, nautical-themed specialty stores, art galleries, and so much more. The following are some of our favorite shops:

1. Chesapeake Trading Company

If you’re on the hunt for a new outfit, head over to Chesapeake Trading Company. This casual yet chic boutique store has a great selection of men’s and women’s apparel, jewelry, home goods, gifts, books, music, and more.

2. Ophiuroidea

Also called “The O” by locals, this coastal-inspired boutique features an array of clothing, handcrafted nautical items, mermaid art, sea glass jewelry, coastal furniture, and home goods. Check them out for one-of-a-kind finds!

3. Simpatico

Foodies will love shopping at Simpatico, a little piece of Italy in the heart of St. Michaels. Here, you can find exclusive “Made in Italy” items such as fine wine, artisan cheeses, meats, olive oils, pasta and risotto, desserts, and much more. They also carry a unique selection of ceramics and gift baskets.

4. Antiques on Talbot

For Eastern Shore antiques, take your time browsing Antiques on Talbot. This famous antique shop features everything from oyster plates and sterling silver to artwork, quilts, linens and more.

5. Silver Linings

Are you looking for a dazzling new necklace or a pair of nautical earrings? Stop into Silver Linings for genuine sterling silver and gemstone jewelry. We especially love the unique Chesapeake Bay-themed collection.

Come Home to Brampton Inn For a Great Night’s Rest

Finally, after a fabulous day trip to St. Michaels, MD, return to our historic Chestertown Inn to relax and unwind. Brampton Inn offers the most romantic and comfortable lodging experience along the Eastern Shore. Located just one hour from St. Michaels, our Inn allows you to see another storybook destination of Maryland during your getaway. Plus, Brampton is just minutes from Chestertown’s best restaurants, shops, and things to do. If you’re looking for luxurious accommodations, top-notch amenities, and delicious food, this is the ideal choice for your getaway!

During your stay at Brampton Inn, you can expect to start each morning right with a delicious, homemade breakfast to send you on your way. After a day of exploring the picturesque town of St. Michaels, kick back and relax in your private room or cottage. Or, join us for our complimentary Afternoon Tea Time and Social Hour.

Are you ready for an unforgettable vacation along Maryland’s Eastern Shore?

Check Availability Now.


Updated March 2024

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