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30 Things to Do in St. Michaels, Maryland (MD)

St. Michaels, Maryland, a charming town located on the Eastern Shore of the Chesapeake Bay, is a perfect blend of maritime history, picturesque landscapes, and quaint Victorian charm. Whether you're an avid history lover, a nature enthusiast, or someone looking for a relaxing getaway, St. Michaels offers a diverse range of activities and attractions that promise to make your visit memorable. This blog explores the unique features of St. Michaels, the best time to visit, unique gems to explore, a suggested day itinerary, and how to reach this enchanting town.

Infographic - 30 Things to Do in St. Michaels, Maryland (MD)

30 Things to Do in St. Michaels, Maryland (MD)

St. Michaels, Maryland, is a charming waterfront town that offers a perfect blend of history, nature, and local culture. Whether you’re an adventure seeker, history enthusiast, or a foodie, St. Michaels offers something for everyone. From exploring maritime heritage to outdoor activities and dining experiences, let’s dive into the best things to do in this scenic location.

1. Explore the Chesapeake Bay Maritime Museum

Short Description of Activity
The Chesapeake Bay Maritime Museum is one of the area’s top attractions. It offers a deep dive into the rich maritime heritage of the Chesapeake Bay and the surrounding regions. The museum features interactive exhibits, historic boats, and outdoor displays.

Pros

  • Engaging exhibits suitable for all ages

  • Opportunity to learn about local history and maritime culture

  • Scenic waterfront location

Cons

  • Can be crowded during peak tourist season

  • Some exhibits may be less interesting for younger children

Key Attractions and Events

  • Working boatyard demonstrations

  • Seasonal festivals celebrating Chesapeake Bay culture

  • Annual OysterFest

2. Visit the 1879 Hooper Strait Lighthouse

Short Description of Activity
Located near the Chesapeake Bay Maritime Museum, the 1879 Hooper Strait Lighthouse is a historic beacon. Visitors can explore its exhibits and climb to the top for beautiful views of the bay.

Pros

  • Historic structure with great photo opportunities

  • Stunning views of the Chesapeake Bay

  • Free entry with museum admission

Cons

  • Limited accessibility for those with mobility challenges

  • May not offer as much to do for those uninterested in history

Key Attractions and Events

  • Guided tours showcasing lighthouse history

  • Special events like lighthouse keeper talks

3. Stroll through the St. Michaels Historic District

Short Description of Activity
The Historic District of St. Michaels is a delightful area to walk, featuring cobblestone streets and quaint buildings. It's full of local shops, art galleries, and restaurants.

Pros

  • Scenic stroll with charming shops and galleries

  • Lots of dining options with local flavors

  • Rich historical architecture

Cons

  • Can be busy during tourist season

  • Some areas may have limited parking

Key Attractions and Events

  • St. Michaels Art League gallery exhibitions

  • Walking tours showcasing the town's history

4. Sail on the Miles River

Short Description of Activity
Take a relaxing boat ride or an active sailing tour on the Miles River. The scenic waterway offers visitors a chance to enjoy the beauty of the Chesapeake Bay and its surrounding landscapes.

Pros

  • Stunning views of the river and surrounding nature

  • Multiple options for boat rentals or guided tours

  • Peaceful, relaxing experience

Cons

  • Limited availability during the off-season

  • Can be expensive depending on the type of tour or rental

Key Attractions and Events

  • Sailing lessons for beginners

  • Sunset cruises for romantic views

5. Attend the St. Michaels Farmers Market

Short Description of Activity
The St. Michaels Farmers Market is a vibrant place where you can find fresh, local produce, artisanal products, and handmade crafts. It’s a great way to immerse yourself in the town’s community.

Pros

  • Support local farmers and artisans

  • Fresh, organic produce available

  • Family-friendly atmosphere

Cons

  • Limited operating hours (usually seasonal)

  • Some items can be more expensive than at regular grocery stores

Key Attractions and Events

  • Cooking demonstrations

  • Local music performances

6. Tour the Classic Motor Museum

Short Description of Activity
For car enthusiasts, the Classic Motor Museum offers a unique glimpse into the history of automobiles. The museum showcases a collection of classic cars and vintage vehicles, telling the story of transportation through time.

Pros

  • Fascinating exhibits for car lovers

  • Well-maintained classic vehicles

  • Interesting for history buffs and families

Cons

  • Might not appeal to visitors who aren’t interested in cars

  • Smaller museum with limited exhibits

Key Attractions and Events

  • Annual car shows and displays

  • Vehicle restoration demonstrations

7. Visit the St. Michaels Museum at St. Mary's Square

Short Description of Activity
The St. Michaels Museum at St. Mary’s Square highlights the town’s history from its founding to its role in the War of 1812. It’s a great stop to learn about the town's past.

Pros

  • Rich historical exhibits

  • Friendly and knowledgeable staff

  • Free admission for a glimpse of local history

Cons

  • Smaller museum with a limited number of exhibits

  • Not much for younger children to engage with

Key Attractions and Events

  • Historical reenactments during special events

  • Guided tours focusing on the War of 1812

8. Enjoy a Meal at The Crab Claw

Short Description of Activity
The Crab Claw is a renowned local seafood restaurant offering fresh Maryland crab and other Chesapeake Bay favorites. It’s an ideal place for seafood lovers to enjoy a casual dining experience.

Pros

  • Fresh seafood caught from the Chesapeake Bay

  • Beautiful waterfront dining with great views

  • Relaxed, family-friendly atmosphere

Cons

  • Can be crowded during peak hours

  • Slightly pricey compared to other local restaurants

Key Attractions and Events

  • Crab feasts and special seafood dishes

  • Seasonal outdoor dining

9. Bike the St. Michaels Nature Trail

Short Description of Activity
The St. Michaels Nature Trail is a peaceful path that lets you enjoy the scenic beauty of the area while getting some exercise. The trail winds through forests, wetlands, and along the Miles River.

Pros

  • Beautiful, natural surroundings

  • Great for cycling, jogging, or walking

  • Ideal for nature lovers and photographers

Cons

  • Can be muddy after rain

  • Not much shade on sunny days

Key Attractions and Events

  • Birdwatching opportunities

  • Annual outdoor fitness events

10. Kayak or Paddleboard on the Miles River

Short Description of Activity
If you're seeking adventure, kayaking or paddleboarding on the Miles River is a thrilling way to explore the local waters. You’ll have the chance to enjoy the natural beauty up close while getting some exercise.

Pros

  • Active outdoor experience

  • Stunning views of the river and surrounding nature

  • Great for both beginners and experienced paddlers

Cons

  • Weather-dependent activity

  • Can be challenging for those with limited fitness or experience

Key Attractions and Events

  • Guided paddling tours

  • Sunset paddleboarding for a unique experience

11. Visit Tilghman Island

Short description of activity:
A short drive from St. Michaels, Tilghman Island is a tranquil, scenic spot that offers beautiful waterfront views, fresh seafood, and an insight into the local watermen’s lifestyle.

Pros and Cons:

Pros:

  • Peaceful and relaxing atmosphere.

  • Great seafood dining options.

  • Excellent location for scenic photography.

Cons:

  • Limited commercial activities.

  • Can be difficult to get to without a car.

Key attractions and events:

  • Tilghman Island’s maritime history.

  • Iconic waterfront views perfect for boat rides or fishing.

  • The famous "Tilghman Island Crab Feast."

12. Attend a Sailing Race

Short description of activity:
St. Michaels is known for its nautical culture, and attending a sailing race is an exciting way to experience the local maritime tradition. Races are hosted regularly, with the Chesapeake Bay providing the perfect backdrop.

Pros and Cons:

Pros:

  • Thrilling event for sailing enthusiasts.

  • Great for spectating along the shore.

  • A chance to learn about local sailing traditions.

Cons:

  • Weather-dependent.

  • Large crowds can make it difficult to find a good viewing spot.

Key attractions and events:

  • The St. Michaels Sailing Regatta.

  • The Chesapeake Bay’s competitive sailing events.

13. Explore Local Art Galleries

Short description of activity:
St. Michaels boasts a vibrant art scene, with a variety of local galleries showcasing works inspired by the town's history and natural beauty. Spend a day strolling through the galleries and discovering pieces by local and regional artists.

Pros and Cons:

Pros:

  • A cultural experience that highlights local talent.

  • Free to browse galleries.

  • Great way to find unique souvenirs.

Cons:

  • May not appeal to everyone, especially if art isn’t your interest.

  • Limited galleries compared to larger cities.

Key attractions and events:

  • St. Michaels Art League.

  • Annual Art Walks in the town center.

14. Take a Ghost Tour

Short description of activity:
St. Michaels is said to be haunted by spirits of the past. Join a ghost tour for a spine-chilling experience that blends history with supernatural folklore. The tours take you through the town's oldest buildings, where stories of hauntings and unexplained events come to life.

Pros and Cons:

Pros:

  • Unique and thrilling experience for those interested in history and the paranormal.

  • Great way to explore St. Michaels at night.

Cons:

  • May not be suitable for young children or those afraid of the dark.

  • Ghost stories are often speculative and may not appeal to all.

Key attractions and events:

  • The Historic Ghost Tour of St. Michaels.

  • Haunted locales such as the Old Inn and the town’s former cemetery.

15. Visit Christ Church

Short description of activity:
Christ Church is an iconic landmark in St. Michaels, offering visitors a peaceful and historic retreat. This Anglican church dates back to 1672 and features beautiful architecture, stained-glass windows, and serene grounds.

Pros and Cons:

Pros:

  • Historical significance with a peaceful atmosphere.

  • Beautiful architecture and stained-glass windows.

  • Quiet place for reflection and photography.

Cons:

  • Limited activities; mostly a site for quiet reflection.

  • May not be of interest to non-history or religious enthusiasts.

Key attractions and events:

  • The beautiful grounds and gardens.

  • Historic graveyard dating back to the 17th century.

16. Enjoy Live Music at Muskrat Park

Short description of activity:
Muskrat Park is the perfect place to enjoy live music on the Chesapeake Bay. This outdoor venue offers seasonal concerts with a mix of jazz, blues, and folk music, providing a perfect atmosphere to unwind while watching the sunset.

Pros and Cons:

Pros:

  • Free live music in a scenic outdoor setting.

  • A relaxed, family-friendly environment.

  • Ideal for an evening picnic.

Cons:

  • Limited performances, depending on the season.

  • Weather can affect the outdoor events.

Key attractions and events:

  • Summer concert series.

  • The scenic view of the bay during sunset.

17. Cross Honeymoon Bridge

Short description of activity:
Honeymoon Bridge is a charming pedestrian bridge in St. Michaels that connects visitors to the nearby park. It’s a perfect spot for a romantic stroll or a leisurely walk with a great view of the water.

Pros and Cons:

Pros:

  • A romantic and scenic spot.

  • Great for photography.

  • Peaceful and tranquil environment.

Cons:

  • Short bridge; may not take long to explore.

  • Can get crowded during tourist season.

Key attractions and events:

  • Romantic walks and photo ops.

  • Views of the surrounding water and wildlife.

18. Visit the Lyon Distilling Company

Short description of activity:
Lyon Distilling Company is a must-visit for craft spirit lovers. Located in the heart of St. Michaels, this distillery offers tastings of its signature rum and whiskey, produced in small batches with local ingredients.

Pros and Cons:

Pros:

  • Great for spirits enthusiasts.

  • Offers tours and tastings.

  • Small, personal distillery atmosphere.

Cons:

  • Not suitable for those who don’t drink alcohol.

  • Limited selection of spirits.

Key attractions and events:

  • Signature rum and whiskey tastings.

  • Distillery tours showcasing the production process.

19. Tour the St. Michaels Winery

Short description of activity:
St. Michaels Winery is an award-winning winery that offers a selection of handcrafted wines made with local grapes. Whether you’re a connoisseur or just a casual wine lover, this is a delightful stop to taste and learn about Maryland’s wine culture.

Pros and Cons:

Pros:

  • Wine tasting experiences with knowledgeable staff.

  • Beautiful vineyard surroundings.

  • Unique local wine selection.

Cons:

  • Not suitable for non-wine drinkers.

  • The winery may be crowded during peak seasons.

Key attractions and events:

  • Wine-tasting tours.

  • The winery’s seasonal events like the wine harvest festival.

20. Attend the St. Michaels Running Festival

Short description of activity:
For fitness enthusiasts, the St. Michaels Running Festival offers a fun and challenging event that includes a marathon, half-marathon, and 5K. The festival is held annually and draws participants from all over the country, offering a scenic course that runs along the stunning waterfront.

Pros and Cons:

Pros:

  • A great way to stay active while exploring the town.

  • Scenic and flat course, ideal for running.

  • Family-friendly event with options for all fitness levels.

Cons:

  • Can be challenging for beginners due to the long distances.

  • The event may be crowded, especially during peak times.

Key attractions and events:

  • The marathon and 5K races.

  • Post-race festivities, including live music and local food vendors.

21. Visit the St. Michaels Mill

Short description of activity:
St. Michaels Mill, a historic gristmill dating back to the early 1800s, is an iconic landmark in the town. This beautifully restored building allows visitors to step back in time and learn about the milling process and the role the mill played in the local economy.

Pros:

  • Educational experience about the town's history.

  • Peaceful setting with scenic views.

  • Great for history buffs and families.

Cons:

  • Limited operating hours.

  • Not much to do beyond the tour.

Key attractions and events:

  • Guided tours explaining the milling process.

  • Nearby walking trails offering views of the surrounding landscape.

22. Experience the Waterman's Wharf Exhibit

Short description of activity:
The Waterman’s Wharf Exhibit showcases St. Michaels’ deep connection with the Chesapeake Bay. This exhibit educates visitors on the local fishing industry and the heritage of watermen in the area.

Pros:

  • Engaging displays and artifacts.

  • Learn about the town’s maritime culture.

  • Family-friendly experience.

Cons:

  • Exhibit can be a bit small, leaving you wanting more.

  • May not appeal to those not interested in maritime history.

Key attractions and events:

  • Permanent exhibit on the town's maritime past.

  • Interactive displays and local artifacts.

23. Attend the Annual Jack Russell Races

Short description of activity:
One of the most unique and lively events in St. Michaels is the annual Jack Russell Races. This quirky event features Jack Russell Terriers racing in heats to determine the fastest pup.

Pros:

  • Fun for all ages.

  • Unique and memorable event.

  • Great way to experience the local community.

Cons:

  • Only happens once a year, so timing is crucial.

  • Can get crowded.

Key attractions and events:

  • Annual races with food vendors and activities.

  • Fun, family-oriented atmosphere.

24. Explore the Frederick Douglass Walking Tour

Short description of activity:
St. Michaels offers a walking tour dedicated to Frederick Douglass, one of the most important figures in American history. This self-guided tour takes visitors to significant locations connected to Douglass’ early life in the area.

Pros:

  • Learn about a key figure in history.

  • Self-guided, so you can explore at your own pace.

  • Rich historical context.

Cons:

  • The tour can be long, requiring some stamina.

  • Limited signage at some stops.

Key attractions and events:

  • Douglass’ birthplace site.

  • Historical markers and points of interest along the route.

25. Visit the Union United Methodist Church

Short description of activity:
Union United Methodist Church is a beautiful church with a history dating back to the 19th century. Visitors can explore its stunning architecture and rich cultural history within the St. Michaels community.

Pros:

  • Beautiful architecture and serene setting.

  • Deep historical and cultural significance.

  • Peaceful atmosphere perfect for reflection.

Cons:

  • Not much to do beyond exploring the church.

  • Limited visiting hours.

Key attractions and events:

  • Sunday services and community events.

  • Historic architecture.

26. Enjoy a Cocktail Cruise

Short description of activity:
Set sail on a relaxing cocktail cruise around St. Michaels and the Chesapeake Bay. These cruises provide a unique perspective of the area’s stunning coastline while enjoying a refreshing drink with friends or family.

Pros:

  • Gorgeous views of the Chesapeake Bay.

  • Relaxing and picturesque experience.

  • Great for romantic getaways.

Cons:

  • Weather-dependent.

  • Can be pricey for larger groups.

Key attractions and events:

  • Sunset cruises with cocktails.

  • Scenic views of the bay and local landmarks.

27. Attend the Annual Christmas in St. Michaels

Short description of activity:
Christmas in St. Michaels is a festive event filled with holiday cheer. The town is beautifully decorated with lights, and various activities include holiday markets, parades, and performances.

Pros:

  • A festive atmosphere full of holiday cheer.

  • Perfect for families and holiday lovers.

  • Numerous events and activities throughout the month.

Cons:

  • The event can be crowded.

  • Limited to the holiday season.

Key attractions and events:

  • Christmas parade and tree lighting.

  • Holiday shopping markets.

28. Visit the Cannonball House

Short description of activity:
The Cannonball House is a historic site that played a role in the War of 1812. This house was hit by a cannonball during the battle, and it has since been preserved as a museum showcasing the area’s wartime history.

Pros:

  • Unique historical significance.

  • Great for history buffs.

  • Small but informative museum.

Cons:

  • The museum is quite small, so it’s a quick visit.

  • Limited to those interested in the War of 1812.

Key attractions and events:

  • War of 1812 exhibits.

  • Preserved artifacts from the era.

29. Shop for Antiques

Short description of activity:
St. Michaels is home to a variety of antique shops offering unique treasures. Visitors can explore these quaint shops and find anything from vintage furniture to rare collectibles.

Pros:

  • Great for collectors and vintage lovers.

  • Many different shops to explore.

  • Locally-owned businesses with unique items.

Cons:

  • Prices can be high for some items.

  • Limited appeal for those not interested in antiques.

Key attractions and events:

  • Antique shops throughout town.

  • Periodic antique fairs and events.

30. Relax at a Local Spa

Short description of activity:
If you’re looking to unwind, St. Michaels has a number of local spas where you can indulge in relaxing massages, facials, and other rejuvenating treatments. Perfect for a tranquil escape.

Pros:

  • Ideal for relaxation and stress relief.

  • Beautiful, serene spa settings.

  • Great way to pamper yourself.

Cons:

  • Can be pricey depending on the spa.

  • Some spas may require advanced reservations.

Key attractions and events:

  • Luxurious spa treatments.

  • Relaxing wellness retreats.

Unique Facts About St. Michaels

St. Michaels is a town steeped in history and culture, making it a must-visit destination for anyone interested in learning about the area’s past and its influence on the present.

Maritime History

Founded in 1672, St. Michaels has long been a hub for the shipbuilding and seafood industries. Its proximity to the Chesapeake Bay played a pivotal role in the town's development, with its shipyards once producing vessels that were crucial to both local and national economies. This maritime heritage continues to influence the town's culture today, from its fishing industry to its well-preserved historic buildings, much like the diverse things to do in Salisbury, Maryland (MD) that showcase the region's rich history and vibrant community.

The Town That Fooled the British

One of the most unique stories associated with St. Michaels dates back to the War of 1812. The town's residents devised a clever strategy to mislead the British navy. During a British raid, townsfolk illuminated trees in a way that made it seem as though the town was more heavily populated than it really was. This trickery earned St. Michaels the nickname "The Town That Fooled the British." It is a testament to the cleverness and resilience of the town’s people during a turbulent time. If you're looking to explore more historical charm, consider discovering things to do in Laurel, Maryland (MD).

Victorian Charm

In addition to its maritime history, St. Michaels is known for its stunning Victorian-era architecture. Many of the buildings in the historic district are beautifully preserved, offering visitors a glimpse into the past with their ornate facades and charming details. These architectural gems provide a picturesque backdrop for exploring the town on foot, just as you'll find unique experiences when searching for things to do in Hagerstown, Maryland (MD).

Best Time to Visit

St. Michaels is a year-round destination, offering different experiences depending on the season. Below is a breakdown of what to expect during each season:

Season Average Temperature Highlights
Spring 50°F to 70°F Blooming gardens, outdoor festivals, and mild weather
Summer 70°F to 85°F Waterfront activities, boating, and vibrant local events
Fall 60°F to 75°F Crisp air, fall foliage, and harvest festivals
Winter 30°F to 50°F Cozy inns, holiday decorations, and winter sales

Spring

Spring offers mild weather, making it an ideal time for outdoor activities. The town’s gardens bloom, and outdoor festivals make the streets come alive. It’s perfect for those who want to enjoy a mix of culture and nature.

Summer

Summer is the most popular time to visit, with warm weather perfect for enjoying St. Michaels’ waterfront activities. Whether you're boating, kayaking, or simply enjoying the vibrant local events, summer brings the town to life.

Fall

Autumn in St. Michaels is characterized by cool, crisp air and beautiful fall foliage. The harvest festivals are a major draw, along with scenic walks along the waterfront.

Winter

Though colder, winter in St. Michaels has its charm. Cozy inns, holiday decorations, and special winter sales offer a peaceful escape from the bustle of larger cities.

Unique Gems to Explore

St. Michaels is home to several must-see attractions, each offering a unique experience that showcases the town's history and charm.

Chesapeake Bay Maritime Museum

A highlight of St. Michaels, the Chesapeake Bay Maritime Museum is an interactive museum that celebrates the region’s maritime history. With historic boats, hands-on exhibits, and educational programs, it’s the perfect place for visitors of all ages to learn about the area’s rich seafaring past.

1879 Hooper Strait Lighthouse

This historic lighthouse, built in 1879, provides a fascinating glimpse into the lives of lighthouse keepers in the 19th century. A visit here not only offers great views of the Bay but also a deeper understanding of the challenges faced by those living and working on the water.

St. Michaels Museum at St. Mary's Square

For history buffs, the St. Michaels Museum at St. Mary's Square is a must-visit. The museum offers exhibits featuring local artifacts and guided tours of the historic district, allowing visitors to immerse themselves in the town’s storied past.

Suggested Day Itinerary

If you’re planning a visit to St. Michaels, here’s a suggested day itinerary that will allow you to experience the best the town has to offer:

Morning: Chesapeake Bay Maritime Museum

Start your day with a visit to the Chesapeake Bay Maritime Museum, where you can explore the interactive exhibits and learn about the region’s rich maritime history. It's a great way to get acquainted with St. Michaels' past and its connection to the Chesapeake Bay.

Lunch: Waterfront Dining

For lunch, head to one of St. Michaels' waterfront restaurants where you can indulge in Maryland's famous blue crab dishes. Many restaurants offer outdoor seating, so you can enjoy a meal while taking in the stunning views of the Bay.

Afternoon: Scenic Boat Tour

In the afternoon, take a scenic boat tour along the Miles River. This relaxing excursion allows you to appreciate the town’s picturesque landscapes and offers a unique perspective of the area’s historic waterfront.

Evening: Historic District Stroll

End your day with a stroll through St. Michaels’ historic district. The quaint streets are lined with boutique shops, galleries, and restaurants. Take your time to browse the local shops and admire the stunning Victorian architecture.

How to Reach St. Michaels, Maryland

St. Michaels is easily accessible by several modes of transportation, making it a convenient getaway.

By Car

St. Michaels is about a 1.5-hour drive from Washington, D.C., via US-50 E. The drive is scenic and offers a great way to experience the beauty of Maryland’s countryside on your way to the Eastern Shore.

By Air

The nearest major airport is Baltimore/Washington International Thurgood Marshall Airport (BWI), which is about a 2-hour drive away. Alternatively, the Easton Airport (ESN) is a smaller airport that is about a 25-minute drive from St. Michaels.

By Boat

Given St. Michaels' maritime heritage, arriving by boat is a popular and scenic option. Several marinas around the town welcome transient dockers, allowing you to dock your boat and explore the town from the water.

Conclusion

St. Michaels, Maryland, combines the charm of a historic town with the vibrancy of modern attractions. From its rich maritime history to its Victorian architecture and scenic waterfront, St. Michaels offers something for everyone. Whether you're looking to explore the past, enjoy delicious local cuisine, or simply relax by the water, this delightful town promises an unforgettable experience. If you're seeking more adventures in the area, consider exploring the unique things to do in Westminster, Maryland (MD).

FAQs

Q1: What is the significance of the 1879 Hooper Strait Lighthouse?

A1: The Hooper Strait Lighthouse is a historic landmark that offers a glimpse into the lives of 19th-century lighthouse keepers. It serves as a museum exhibit where visitors can learn about the lighthouse's history and its role in the region's maritime past.

Q2: Are there outdoor activities available in St. Michaels?

A2: Yes, St. Michaels is a hub for outdoor activities. Visitors can enjoy boating, fishing, kayaking, biking, and hiking, taking full advantage of the town’s scenic trails and waterfront location.

Q3: What are some annual events in St. Michaels?

A3: St. Michaels hosts several annual events, including the St. Michaels Running Festival, the Fourth of July fireworks, and the "Fall into St. Michaels Weekend," which features the popular Jack Russell dog race.

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