20 Best Things to Do in St. Michaels, MD

St. Michaels, MD
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Located in the heart of Talbot County, Saint Michaels is a charming town featuring over 300 years of history.

Saint Michaels is more than just a place where you spend some nights; it's an event in itself!

It offers all the modern amenities you need to make any weekend getaway an island adventure for the whole family.

Its closeness to Washington (only an hour away) makes St. Michaels your best vacation destination on the Chesapeake for all seasons.

If you're looking for awesome things to do in St Michaels, MD, check out these top destinations and activities that you'll certainly enjoy:

Get Up Close to Maryland's Past With Chesapeake Bay Maritime Museum Tour

Daytime view of Chesapeake Bay Maritime Museum
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Wonderful museums like Chesapeake Bay Maritime Museum take you on a journey of discovery.

The CMBM has over 18 acres of the exhibit, meeting space, and events covering an amazing array of maritime history and tradition!

If you love water, boats, and all things nautical, you'll definitely want to visit this place.

There are captivating events, free activities, programs for kids, vacations, special exhibits, and so on.

Exterior of Chesapeake Bay Maritime Museum
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You'll also find the preserved 19th-century Hooper Strait Lighthouse here.

The Chesapeake Bay Maritime Museum is also fantastic at stocking arguably one of the best South Maryland gift shops.

All these things make this wonderful museum a must-see!

A boat docked at Chesapeake Bay Maritime Museum
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Take a Dip and Play Frisbee at Muskrat Park

Located on a welcoming peninsula just minutes from the city, Muskrat Park is a haven for two and four-legged friends alike.

A grassy knoll with brick-lined walking paths winds through a lush, pet-friendly landscape of trees, lawns, and gardens.

Meander along shaded trails lined by blossoming flowers in bloom during summer months.

Hang out in the colorful gazebo to take in panoramic views of the scenic harbor.

Visit the Lyon Rum Distillery and Take Home a Barrel of the Finest Spirit

If you're looking for high-quality, handcrafted spirits that will no doubt impress the senses as well as your guests, take a walk at Windon Distilling!

From the moment you walk up to the old factory Windon Distilling,  it becomes immediately clear that there is a lot of love and care that goes into everything they do.

It's hard not to love all the hard work that went into producing such a high-quality product.

Lyon Rum is the first step in Windon Distilling Company's journey to crafting unique, handcrafted spirits brewed right here on Maryland's eastern shore.

Launched in 2012, the distillery has made a prominent name for itself by working to define what American rum can be, all while experimenting with inspired and unique finishes.

The distillery's flagship spirit passes through the hands (& palates) of team members who worked diligently to ensure each new batch maintains an authentic taste that helps it stand out above other spirits out there.

When an artist is passionate about their work, they are willing to go the extra mile.

Hopkins Art Gallery is all about art, featuring a fantastic collection of artwork from modern and coastal artist Ryan Hopkins.

In addition to promoting the artist's work, the gallery also offers other products, including classic vinyl records for sale and original pieces from the same artists.

If art and music are your things, you'll be able to find something you enjoy among Hopkins Art Gallery's many offerings.

See Classic Cars From 1931 to 1945 at the Classic Motor Museum

When you walk through the door, you're immediately assaulted with an amazing collection of vintage cars from an era when American engineering was the best in the world.

It features vintage cars with old-fashioned charm and plenty of horsepowers, as well as motorcycles and trucks that will make your jaw drop.

They have a classic Mustang and Blue Devil that are both restored to perfection.

In addition to these amazing automobiles, there is also a quaint cottage house featuring everything from original artwork to antique decorations and genuinely historic photographs from the 1960s.

Filled with rustic antiques and affectionate old stories about the American way of life, this museum will make your $10 admission fee worth it tenfold.

Head to Ava's Pizzeria & Wine Bar for Crispy Salads & Great Pizzas

In Ava's Pizzeria & Wine Bar, everything is top-notch!

The service is friendly and efficient, the fries are delicious, the salads tasty, the meatballs impressive, and their pizzas something special.

The garden seating is charming, with beer taps as water features.

While they pack a lot of flavor into their pizzas, Ava's meatball sub is also great because it comes with homemade quality meatballs.

This restaurant serves some seriously fresh food at excellent prices, so it's perfect for casual dining on any given day.

Cruise in Style With Patriot Cruises

A docked boat of Patriot Cruises
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Enjoy the waterfront with a narrated cruise aboard the Patriot!

Traveling on the scenic Miles River and the Chesapeake Bay, you'll have plenty of time to enjoy the view as you sail past historic St. Michaels and past quaint village shops and restaurants lining Main Street.

Don't worry about being late; you can make reservations for chartered tours of up to 145 people!

A point of particular interest is that rooms are available for large groups or families to rent at various prices that depend on size and location.

In addition, parking is free!

Groups will have a tour guide who will make sure everyone behaves during their harbor tour.

In case your kids get restless, don't worry - entertainment abounds in this relaxing 75-minute harbor cruise, complete with air conditioning, live music, waterside seating, and multiple restrooms.

Enjoy the View in Hollis Park

When you're on vacation with your family, it's easy to get caught up in the busy day of touring around at your destination.

However, there are moments when everyone needs a little break to gather their thoughts and collect themselves for the next activity ahead.

Hollis Park is exactly where you need to go to take a step back and breathe some fresh air.

Whether you're with an infant or toddler, this dog-friendly 2-acre public park is perfect for taking a moment of peace away from the everyday hustle & bustle.

And for those with young children who still like to run around endlessly, Hollis Park has all kinds of attractions, including swings, slides, and climbing bars.

You'll find Hollis Park nestled between Town Hall and the Chesapeake Bay Maritime Museum.

Shop Exquisite Designer Jewelry for Less at DBS Fine Jewelers

DBS Fine Jewelers is an awesome jewelry store.

They have many different rings and necklaces that they offer in front of their store for you to look through and try on.

It's a nice place to shop around for some gifts, including watches, wedding dresses, bracelets, glasses, earrings, charms, and more!

It's doubtful you will find another shop in town with an exciting combination of collections at comparable prices.

Visit 208 Talbot Restaurant for Exceptional Cuisine

If you've been looking for a place to dine at St. Michaels, then look no further than 208 Talbot Restaurant!

208 Talbot puts up a quality of food and beverage that's entirely true of the best restaurants not only in Baltimore but all across the East Coast.

This gem of a restaurant offers delicious food that will transform your dining experience.

You can expect nothing less than both exceptionally flavorful dishes and an expansive wine list that you wouldn't find anywhere else on Shore.

And the ambiance is quaint and inviting, and the staff will go out of their way to ensure you have a lovely experience here.

Buy a Piece of History at Iron Will & Woodworks

History is fascinating, and you're going to love the way Mark and Tracey Miller at Iron Will & Woodworks choose to use it as their primary focus.

You can find Iron Will & Woodworks in the historic downtown area of St. Michaels, Maryland, but they're now in 1007 S. Talbot St.

The lovely yet straightforward shop offers many reconstructed pieces, such as doors, windows, arches, railings, and battens.

Much research goes into each piece of salvage, rare wood slab, antique, and vintage furniture carefully selected by Iron Will & Woodworks.

There is a certain charm in finding something that sparks memories of good times past in various people.

At Iron Will & Woodworks, the company does its best for each product to represent what it stands for.

Bike, Paddleboard, or Kayak With Shore Pedal & Paddle

St Michaels locals' and visitor's favorite spot for fun on the water is Shore Pedal & Paddle, located in the heart of St. Michaels, Maryland.

The canoe & kayak rental service offers a great selection of rentable goods that will help you have a great time while visiting the beautiful town of St Michaels.

They offer a full range of products and services from rentals, tours, instruction, and sales.

Shore Pedal & Paddle has a floating dock at the Marina and a kayak launch near San Domingo Creek.

If you're looking to get out there on the water or want to learn how to get certified, then SP&P should be your go-to for all water-related things!

Their season can extend from April 1st - October 31st, but please confirm with them before you plan your trip if you're visiting over spring break or around another holiday weekend or event!

Eat Fresh Seafood at the Crab Claw Restaurant

Located in Navy Point, The Crab Claw Restaurant was initially known as "The Eastern Shore Clam Company."

It all began when local watermen lent their catch of oysters, clams, or crabs to families who weren't always able to harvest seafood themselves.

What makes this restaurant also the best in town is the customer service; they go out of their way to make you feel welcome whenever you walk through their doors!.

If you haven't tried out their crab dip yet, you have to when you find yourself in St Michaels.

It's so delicious it may just become your new favorite thing!

Go on a Romantic Chesapeake Bay Sailing Tour With Sail Selina II

Want to escape the stress of your day-to-day life and enjoy some time on the Chesapeake Bay?

Take a two-hour yacht tour with Selina II out on St Michael's waters.

This intimate catamaran is designed for six guests, so whether you're cruising with family or friends, you can expect an experience of leisure, relaxation, and all-encompassing relaxation!

Enjoy one of the most unique and extraordinary boat tours available on the region's beautiful waterways.

The luxury sailboat Selina II offers an intimate two-hour tour on one of the areas' finest historical catboats, which was meticulously restored to her original grace and beauty.

So if you're itching for a cruise, then Selina II is definitely the yacht you need to consider visiting for an unforgettable experience.

Feel at Home at the Inn at Perry Cabin

Exterior of the Inn at Perry Cabin
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One of the most prestigious resorts on Maryland's Eastern Shore is The Inn at Perry Cabin near St. Michaels.

You may roam around, discover, or just relax on a bench and let the water flow past.

Indulge your body and spirit at Perry Cabin's spa.

Enjoy the range of health activities our fitness facility offers, from a Peloton workout to yoga by the Miles River.

Get additional space to relax and enjoy the Eastern Shore's natural beauty.

Snuggle up in plush recliners in the privacy of your own home space.

For a genuinely unforgettable dining experience, treat your taste buds with seasonal options and the finest food from the Eastern Shore, served waterside.

Delight in Sweet Treats at Justine's Ice Cream Parlor

National publications and newspapers posted articles about Justine's Famous Wall of Shakes.

They have developed over 35 distinctive shakes over more than 30 years.

Justine's Ice Cream Parlor currently provide more than 77 traditional and specialty milkshakes.

Ice cream sodas from Justine's Ice Cream Parlor are old-fashioned.

Whipped cream and a cherry are placed on their handcrafted 24-ounce soda.

You may choose from a wide selection of ice cream flavors.

Toppings like chocolate sprinkles, Reese's pieces, Oreos, M&Ms, hot fudge, chocolate syrup, marshmallows, and more are available as dry and wet toppings.

Toast a Glass of Wine with Friends at Great Shoals Cellars

The Great Shoals Light, which formerly stood near the Wicomico River's mouth, inspired the name of Great Shoals Cellars.

Their main source of grapes is a Queen Anne's County vineyard.

They choose the best local orchards for their apples, pears, berries, and other fruits.

Great Shoals Cellars take great pride in working with Maryland farmers to acquire the freshest fruits to make the greatest wines and hard ciders in the state.

They provide small plate meals with refreshments and sample flights of wines and ciders.

Additionally, each wine is offered in a glass or bottle.

Planning a gathering? Great Shoals Cellars offer a pleasant and cozy setting, making it ideal for any event.

Admire the View while Drinking at Bistro St. Michaels

Since it opened, Bistro St. Michaels has offered traditionally prepared food with seasonal influences in a welcoming setting.

The Bistro has consistently been a favorite with both locals and tourists.

Their seasonal restaurant menus discover texture, color, and supreme flavors.

Their chefs thoughtfully choose every item, sourcing all of their vegetables, meat, and seafood from local, sustainable sources with a focus on helping out local farmers and craftsmen.

The front porch, the chef's counter, the conventional indoor table seating, and the garden terrace are just a few available seating arrangements.

At their Chef's Counter, you can see the culinary staff in motion while dining in the open kitchen!

Relax for a Day at the Spa at Harbour Inn

A little refuge called The Spa at Harbour Inn is on the third floor.

Six treatment rooms, including solo massage rooms, facial rooms, and a room for couples, are available at the spa.

A little store in the reception area sells an array of items, including expert skincare products for the body and face.

If you just want to look around or need a quick present, you are welcome to stop by.

The modest yet cozy relaxation area is great for unwinding before or after your session.

A selection of herbal teas, enriched spa water, wine, and snacks are available.

The hotel has a lovely view of a modest port where, during the fishing season, you can observe local watermen returning with their day's catch.

Final Thoughts

St Michaels offers some of the most pristine views around, and there are plenty of ways to appreciate them to your heart's content.

While wandering through St Michaels, you can enjoy any number of outdoor activities.

From hiking to kayaking, St Michaels has it all.

Then again, maybe you'd like to spend an afternoon browsing the many quaint shops or relax with the family at one of the charming eateries or pubs.

With all its gorgeous natural scenery and fun-filled activities not far from home, St Michaels will make for an unforgettable vacation.

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