St. Michaels, MD: The Best & Fun Things To Do (Plus Places To Visit If You’re Feeling Fancy)

St. Michaels, MD: The Best & Fun Things To Do, St. Michaels, Maryland

This town is flat and small enough to cover on foot or on two wheels. The Rails-to-Trails bike path runs straight through the middle of the place. The maritime museum sits on an 18-acre waterfront campus that you can walk. Talbot Street lines up its shops and boutiques along a single stretch of road. And the water is never far away from wherever you happen to be standing.

Welcome to St. Michaels, Maryland. This small town on the Eastern Shore of the Chesapeake Bay suits a weekend getaway or a day trip. With its deep history, its waterfront views, and its unusual shopping and dining, St. Michaels covers a lot of ground.

Land Adventures in St. Michaels: Take a walk through the historic district of the town and take the architecture of the 19th century homes. Visit the Chesapeake Bay Maritime Museum to pick up the maritime heritage of the town and work through the 18-acre waterfront campus. Rent a bike and ride along the scenic Rails-to-Trails bike path that runs through St. Michaels.

Sea Excursions: Take a sunset cruise on the Chesapeake Bay or rent a kayak and work the Miles River. Charter a fishing boat and try your luck at catching some of the well-known blue crabs of the bay. Whatever your nautical preference, St. Michaels runs plenty of options to satisfy it.

Key Takeaways

St. Michaels offers a variety of land and sea adventures for visitors to enjoy.
The town’s maritime heritage is celebrated at the Chesapeake Bay Maritime Museum.
From sunset cruises to kayak rentals, there are plenty of ways to explore the Chesapeake Bay and its surrounding waterways.

Welcome to St. Michaels, Maryland

Ahoy there, matey. Welcome to the waterfront town of St. Michaels, Maryland. You are in for a good one, because this place is full of things to do. History buff, someone who eats well, or just after a quiet getaway, St. Michaels has you covered.

First things first, let us talk about the town itself. St. Michaels is a picturesque little town on the Eastern Shore of Maryland. It is known for its waterfront views, its small shops, and its historic landmarks. And let us not forget the seafood. This town suits anyone who takes to it, with plenty of restaurants serving fresh catches from the Chesapeake Bay.

One of the stronger things about St. Michaels is that it is a good place to just wander and work through. The streets are lined with small shops and galleries, and there are plenty of historic buildings to take in. And take the Chesapeake Bay Maritime Museum, which works to preserve the history and culture of the Chesapeake Bay.

For a little more pace, there are plenty of outdoor activities to take in St. Michaels. Take a boat tour of the bay, go kayaking or paddleboarding, or try your hand at fishing. And if you are feeling brave, you can take a dip in the bay (just watch out for jellyfish).

Whatever you are interested in, you will turn up something to do in St. Michaels, Maryland. So what are you waiting for? Grab the sunscreen and your sense of adventure, and let us go and work through this waterfront town.

Land Adventures in St. Michaels

You may think that St. Michaels is all about water activities, but there are plenty of land adventures here too. History buff, nature lover, or just after some exercise, St. Michaels has a version of each.

First up, the trails. St. Michaels is home to several strong trails for hiking, biking and walking. Some of the busier ones include the St. Michaels Nature Trail, the Rails to Trails, and the Tilghman Island Trail. These trails open out over the Chesapeake Bay and the surrounding countryside, and they turn up plenty of wildlife. Just be sure to bring the bug spray.

If history interests you more than nature, St. Michaels runs plenty of historic sites to work through. One of the busier ones is the Chesapeake Bay Maritime Museum, which gives you the history of the Chesapeake Bay and the people who have lived and worked on its shores. You can also visit the St. Michaels Museum at St. Mary’s Square, which tells the story of the founding and growth of the town over the years.

And no visit to St. Michaels is complete without a visit to one of its many parks. The largest and busiest is probably the St. Michaels Community Park, which runs everything from playgrounds and ball fields to picnic areas and walking trails. There is also the Perry Cabin Park, which is home to the well-known Inn at Perry Cabin and opens out over the Miles River.

So for a slow walk through the country, a deep run at local history, or just a day out with the family, St. Michaels has plenty on land as well as on the water.

Sea Excursions

Ahoy there, matey. In St. Michaels you cannot miss the chance to take the water on a boat, sail, kayak, canoe, or even a stand-up paddleboard. The Miles River is a good place to start, and you can rent a boat or kayak at the Chesapeake Bay Maritime Museum.

Fishing enthusiasts can join a fishing trip on the Selina II, a 1926 sailing yacht. You can also take a water taxi to work the area or go on a sunset sail.

Feeling bold? Rent a jet ski and take off across the water. But be careful, because you do not want to end up in the drink.

However you choose to take the sea, bring sunscreen, a hat, and plenty of water. And do not forget to keep an eye out for dolphins and other sea creatures.

The Maritime Experience

Ahoy. Anyone who takes to all things nautical is in luck, because St. Michaels is chock-full of maritime experiences that will float your boat.

First up, the Chesapeake Bay Maritime Museum (CBMM), one to see for anyone interested in the history and culture of the Chesapeake Bay region. This museum holds a vast collection of marine artifacts, alongside exhibits on shipbuilding and the ecology of the Bay. And take the Hooper Strait lighthouse, which has been carefully restored to its former standing.

Speaking of shipbuilding, did you know that St. Michaels was once a hub for boat construction? The shipbuilding heritage of the town is on full display at the St. Michaels Museum, where you can see examples of small boats that were built in the area.

To get out on the water yourself, there are plenty of options. The Selina II is a sailboat that runs public and private charters, while the marinas in town can hook you up with everything from kayaks to powerboats.

And no maritime day is complete without a taste of rum. Head to Lyon Distilling Company to sample some of their award-winning spirits, their dark rum among them, which is aged in barrels that once held Hooper Strait Lighthouse bourbon.

So hoist the mainsail and set a course for St. Michaels, because you are in for a maritime run that stays with you.

Art and Antique Hunting

St. Michaels is strong ground for art and antique lovers. You will find everything from galleries to antique stores to unusual shops and boutiques.

If you’re an art enthusiast, there are several art galleries in St. Michaels that you can visit. The Foundry Art Centre is a great place to start. You’ll find a wide range of artworks, from paintings to sculptures to mixed media. The gallery also hosts workshops and events, so be sure to check their schedule before you go.

For antique hunters, St. Michaels is a paradise. You can find everything from artifacts to antique furniture to retro toys. If you’re looking for antique shops, check out Antiques on Talbot. They have a wide selection of antiques, including furniture, glassware, and vintage clothing.

If you’re looking for something unique, check out the Historic Burlington Antiques Emporium. They have retired amusement park fixtures, military collectibles, and retro toys. Who knows, you might even find something you didn’t know you needed!

For art and antique lovers, St. Michaels is the place. So put on the walking shoes, grab the wallet, and get ready to hunt.

Tasting St. Michaels

You cannot visit St. Michaels without taking some of the local flavors. The town is home to a spread of wineries, distilleries, and breweries that run tastings and tours.

Start off at St. Michaels Winery, where you can sample premium boutique wines that reflect the Chesapeake Bay. Their tasting room is warm and inviting, and the staff know their ground. And do not miss their Chardonnay or Cabernet Franc.

For something stronger, head over to Lyon Distilling. This small-batch distillery works in rum and rye whiskey, and their products are made with locally sourced ingredients. Their tasting room sits in a historic building and keeps a laid-back feel.

Beer lovers should take Eastern Shore Brewing. This microbrewery runs a spread of craft beers, their well-known St. Michaels Ale among them. Their taproom is a good spot to sit down with friends over a cold one.

And no trip to St. Michaels is complete without some of the local seafood. The Crab Claw is a busy spot for Maryland blue crab, and its waterfront position opens out over the harbor. For oysters, head over to the tasting room at Great Shoals Cellars. They run a spread of oyster pairings with their wines, and the staff will point you to the right match.

So for wine, whiskey or beer, St. Michaels has a version of each. And do not forget to take some of the well-known seafood of the town while you are at it.

Retail Therapy on Talbot Street

Are you in the mood for some serious shopping? Talbot Street in St. Michaels, Maryland is the answer. This small street is lined with unusual shops and boutiques, running everything from clothing to antiques to toy stores.

Anyone who takes to vintage finds should stop by the antique stores on Talbot Street. You never know what you might turn up. And for a new outfit, there are plenty of clothing boutiques to choose from.

But it is not only about the shopping. Talbot Street is also home to some genuinely fun stores. If you have kids (or are just a kid at heart), take the toy stores. You will find everything from stuffed animals to puzzle games to keep you occupied for hours.

So next time you are in St. Michaels, take a walk down Talbot Street for some retail therapy. You will not go away disappointed.

The Classic Motor Museum

Car enthusiasts will want to take the Classic Motor Museum in St. Michaels. This museum works to appreciate and preserve the heritage of America in automotive innovation and adaption.

Inside, you will find a collection of classic cars, vintage trucks, and motorcycles. The current exhibit runs strong examples of Pre- and Post-WWII classic automobiles, and mid-century muscle cars.

You do not have to be a gearhead to take to these classic cars. Even if you do not know a carburetor from a crankshaft, the clean lines and shiny chrome will hold you.

The museum works well for the whole family. Kids will take to getting up close with these classic cars, and parents will take to reliving their youth.

So for a classic car aficionado or just a family afternoon, the Classic Motor Museum is worth the walk.

The water sets the pace in this town and it never seems to hurry. Boats go past the harbor tables the whole time you are eating. The Selina II is a sailing yacht that was built back in 1926. Tilghman Island is a sleepy fishing village a short way down the road. And the summer concert series plays while the sun goes down over the water.

Local Brews and Spirits

You cannot visit St. Michaels without taking some local brews and spirits. The town is home to some of the finer breweries and distilleries in Maryland, and they are worth the time.

Craft beer people should head over to Eastern Shore Brewing. This local brewery has been serving beers since 2008. They run a broad spread of brews to choose from, their well-known St. Michaels Ale among them. Trust us, one sip of this beer and you will be back.

For something a little stronger, take Lyon Distilling. This small-batch distillery works in rum and whiskey. Their rye whiskey is the one to order, and their dark rum suits a chilly evening. And their tasting room is warm and inviting, which makes it a good spot to sit down after a long day working through the town.

Looking for something genuinely out of the ordinary? Take the Distillery at The Winery. This family-owned distillery produces small-batch spirits using grapes from their vineyard. Their brandy stands out, and their gin is infused with local botanicals for a proper Eastern Shore flavor.

Wherever you go, you will find strong drinks and a friendly room. So go ahead, raise a glass to St. Michaels and everything it runs. Cheers.

Exploring the Eastern Shore

So you are in St. Michaels, Maryland, and you are looking for things to do and places to visit. Lucky for you, the Eastern Shore has plenty.

First up, we have Oxford. This small town is a short drive from St. Michaels and repays the visit. Take a walk down the quiet streets and take the historic homes, or head down to the marina and watch the boats go by.

Next, we have Cambridge. This waterfront city is home to some strong restaurants and shops, alongside a deep history. Take the Harriet Tubman Museum and Educational Center to pick up the Underground Railroad and the men and women who risked everything to help slaves escape to freedom.

For some outdoor ground, head to Stevensville and work through the Chesapeake Bay Environmental Center. This 510-acre wildlife preserve runs hiking trails, kayaking, birdwatching, and more.

For a dose of small-town character, take Chestertown. This historic town is home to Washington College, alongside a number of art galleries, antique shops, and restaurants. And do not miss the annual Chestertown Tea Party Festival, where locals reenact the well-known Boston Tea Party.

Last but not least, we have Tilghman Island. This sleepy fishing village suits slowing down and doing very little. Take a scenic drive along the waterfront, or rent a bike and work the island on two wheels.

So there it is, a few of the places to visit on the Eastern Shore. History, adventure, or just some good old-fashioned time doing nothing, the Eastern Shore has a version of each.

Nearby Cities to Visit

So you have worked through the things to do and places to visit in St Michaels, Maryland, and you are ready for more? Lucky for you, there are some strong cities nearby that repay the drive.

First up, we have Annapolis. This small city sits about an hour of driving from St Michaels and is known for its harbor and its historic architecture. Anyone who takes to seafood will want to work through the many seafood restaurants in Annapolis. And history people can visit the United States Naval Academy or take a walk through the historic district.

Next, we have Baltimore. About an hour and a half of driving from St Michaels, Baltimore is a busy city with a lot to offer. Sports people can catch an Orioles game at Camden Yards or a Ravens game at M&T Bank Stadium. Art lovers can visit the Baltimore Museum of Art or the Walters Art Museum. And for good food and drinks, take the many bars and restaurants in the Fells Point neighborhood.

Last but not least, we have a few other nearby cities worth mentioning. Easton, Maryland is only about a 20-minute drive from St Michaels and has a small downtown area with plenty of shops and restaurants. Cambridge, Maryland is about a 45-minute drive and is known for its waterfront views and its historic district. And if you are willing to go a little further, Washington D.C. is about a two-hour drive and runs attractions without end.

So there it is, plenty of nearby cities to visit when you are done with St Michaels. Just remember to bring your sense of adventure and your appetite for good food.

Holiday Celebrations in St. Michaels

You are in for a good one if you happen to be in St. Michaels during the festive season. This small town knows how to celebrate the season properly, and there are plenty of events to take.

One of the stronger parts of December in St. Michaels is the Christmas in St. Michaels celebration. This event runs across the early days of December and covers a spread of activities and events. You can take a tour of the historic homes of the town, take a Christmas parade, and shop for unusual gifts at the Christmas bazaar. And do not miss the gingerbread house display, which runs serious creations from local bakers and chefs.

For an unusual way to celebrate Christmas, consider taking a festive cruise on the Patriot. This boat tour takes you around the Miles River and St. Michaels Harbor while you take seasonal music and warm treats. Be sure to bundle up, though, because it gets chilly out on the water.

There are plenty of other festive events to take in town beyond Christmas in St. Michaels. The Chesapeake Bay Maritime Museum hosts a December festival, complete with live music, crafts, and a visit from Santa Claus himself. And for a special seasonal meal, many of the restaurants in St. Michaels run special menus and events throughout the season.

St. Michaels holds up as a place to celebrate at the end of the year. With its Main Street, its historic homes, and its festive events, the mood of the season will find you during the visit.

Outdoor Concerts and Events

St. Michaels is a good place to take live music outdoors. Classical, jazz or rock, there is a version of each.

One of the busier events is the St. Michaels Brewfest, which runs every June. It features over 100 craft beers, food trucks, and live music. It suits a summer day in St. Michaels.

For something a little more laid back, take the Summer Concert Series at the Chesapeake Bay Maritime Museum. You can bring a picnic and take the music while watching the sunset over the water. It is like having your own private concert, with better scenery.

Classical music lovers should take the Chesapeake Chamber Music Festival. Held every June, it features musicians of the first rank playing in small settings throughout St. Michaels. It is a good way to take classical music up close.

And if you are in town during the 4th of July, do not miss the fireworks and live music at the St. Michaels Fireworks Celebration. It suits celebrating the birthday of America with some strong tunes at the same time.

So grab a blanket, some snacks, and your dancing shoes, and get ready for some outdoor music in St. Michaels.

Relaxation and Wellness

After a long day working through the town, you might need some rest. St. Michaels runs a spread of options for you to de-stress and slow down.

If you need a spa day, Linden Spa is the answer. This luxurious spa runs a spread of services, massages, facials and body treatments among them. Take a hot stone massage or a hydrating facial, and leave feeling refreshed.

For something a little more out of the ordinary, why not try a yoga class? There are several yoga studios in St. Michaels, running classes for all levels. Seasoned yogi or beginner, you will find a class that suits.

And to really slow down, why not spend some time on the water? Take a slow kayak or paddleboard trip and take the sun and fresh air. It works the body and it clears the head at the same time.

Whatever your idea of rest is, St. Michaels has a version of it. So go ahead, take a day for yourself, because you have earned it.

St. Michaels’ Unique Dining Experience

You cannot visit St. Michaels, Maryland, without trying some of its dining. From seafood to pizza, this small town covers a lot of ground. Here are the places to eat in St. Michaels:

Foxy’s Harbor Grille

For a casual meal, Foxy’s Harbor Grille is the place. With its outdoor seating over the harbor, you can eat while watching the boats go by. Their menu runs a spread of seafood dishes, burgers and sandwiches, alongside vegetarian options. And do not forget to try their well-known crab cakes, which are made with jumbo lump crab meat and seasoned properly.

Bistro St. Michaels

For a more upscale meal, head to Bistro St. Michaels. This French-American restaurant runs a warm and quiet room, which suits a date night or a special occasion. Their menu runs classic French dishes like steak frites and mussels, alongside American favorites like burgers and salads. And save room for dessert, because their profiteroles hold up.

Ava’s Pizzeria & Wine Bar

For pizza, Ava’s Pizzeria & Wine Bar is the place. Their wood-fired pizzas are made with fresh ingredients and cooked properly. They also run a spread of salads, sandwiches, and pasta dishes. And there is their extensive wine list, which runs both local and international wines.

Wherever you choose to eat in St. Michaels, the meal will hold up. So grab a fork and get on with it.

Frequently Asked Questions

What are some fun activities to do in St Michaels that won’t break the bank?

St. Michaels is full of activities that will not break the bank. Take a walk through the small streets and take the historic architecture. Visit the Chesapeake Bay Maritime Museum, which waives the entry charge on certain days of the year. Or head to the St. Michaels Winery for a free wine tasting.

Where can I find the best seafood in St Michaels?

You cannot go wrong with seafood in St. Michaels. Head to the Crab Claw for some of the freshest crab cakes in town. Or try the Carpenter Street Saloon for their well-known oysters. For a more upscale meal, the Inn at Perry Cabin runs a strong seafood menu.

What are some unique events or festivals that happen in St Michaels?

St. Michaels hosts a spread of events and festivals throughout the year. Do not miss the St. Michaels ChocolateFest in February, the St. Michaels Running Festival in May, or the St. Michaels Wine Festival in September. And the annual St. Michaels Christmas parade is one to see.

For a warm and quiet place to stay, the Old Brick Inn is the answer. This historic bed and breakfast runs well-appointed rooms and a strong breakfast. Or try the Black Walnut Point Inn, which opens out over the water.

What’s the best way to see St Michaels – by land or by sea?

Why choose when you can do both? Take a scenic boat tour to see St. Michaels from the water, or rent a bike to work the town on land. And do not forget to take a walk along the waterfront to take the views.

Is it true that St Michaels has a secret underground tunnel system?

We are not sure if it is true, but we like to think so. Legend has it that St. Michaels holds a secret underground tunnel system that was used by smugglers during the Prohibition era. Keep your eyes peeled for any mysterious trapdoors or quiet passageways.

Frequently asked questions about St. Michaels, Maryland

Which maritime museum here is worth giving a whole morning?

The Chesapeake Bay Maritime Museum, straight away. It sits on an 18-acre waterfront campus and holds a vast collection of marine artifacts, exhibits on shipbuilding, and the carefully restored Hooper Strait lighthouse. The smaller town museum covers the founding story of the place instead. That one shows examples of the small boats that were built in this area. You can also rent a boat or a kayak at the maritime museum.

Which local distillery here is worth stopping into for a taste?

Lyon Distilling Company, without hesitation. The small-batch distillery works in rum and rye whiskey made with locally sourced ingredients, and its tasting room sits in a historic building with a laid-back feel to it. Their dark rum is aged in barrels that once held bourbon. Eastern Shore Brewing has been pouring craft beer since 2008 instead. The winery in town runs premium boutique wines as the third option.

Which trail here suits a bike ride through the town?

The Rails to Trails path, first choice. It runs through the middle of the town, opens out over the Chesapeake Bay and the surrounding countryside, and turns up wildlife along the way. The nature trail is the shorter walking option closer in instead. The Tilghman Island Trail sits further out along the road from here. Bring bug spray whichever one of the three you end up taking.

Keep exploring St Michaels, Maryland