Things To Do: A Weekend in St. Michaels, MD with Kids

Maryland is full of little gems of a town. It’s a wide state with far more to offer than many people realize. Want to spend a weekend in the mountains? Maryland has them. Want a weekend on the beach? Maryland is a great option! Want a glimpse of history? Maryland definitely has that. Want to fall in love with an adorable coastal town? You will find plenty in Maryland. One of my favorite little towns is on the Eastern Shore, and I am excited to share all the best things I can do in St. Michael’s, MD. 

Growing up, I never realized how blessed I was to grow up in a state that had so much to offer. We were a short drive to Philidelphia, the Delaware Beaches, and even New York City. It’s a really great home base from which to explore many places on the East Coast. While it wasn’t where I wanted to spend the rest of my adult life, I’ll forever be thankful for growing up in Maryland. 

Nestled on the serene shores of the Eastern Shore of Maryland, St. Michaels is a charming, historic town that offers a relaxing getaway for families. Voted one of the top 10 best small towns in the USA. With its maritime history, quaint streets, and beautiful waterfront views, this coastal gem provides a laid-back atmosphere that’s perfect for a family trip. Whether you’re looking for hands-on learning experiences, outdoor adventures, or peaceful moments by the water, St. Michaels has something for everyone. I remember my very first trip to St Michael’s was by boat when I was maybe 8; we tied up and docked for the night and had such a fun time- it’s a very memorable and charming town. 

About St. Michaels

St. Michaels is a small town located on the Chesapeake Bay, steeped in rich maritime history. Known for its seafood, historic sites, and coastal charm, the town offers a slower pace compared to more bustling tourist destinations. The town is home to the Chesapeake Bay Maritime Museum, numerous restaurants featuring local seafood, and unique shops and galleries that line the main streets. St. Michaels is an ideal destination for families looking for a peaceful escape while exploring the natural beauty and history of the region.

The area is cinematically famous for its presence in The Wedding Crashers, which took place at a beautiful inn.

How Long to Stay in St. Michaels

A 2-3 day weekend trip is the perfect length for a family visit to St. Michaels. This allows time to explore the town’s main attractions, spend some time on the water, and enjoy leisurely walks around the quaint streets without feeling rushed. For families who want to extend their stay and explore the surrounding areas, a 4-5 day trip is ideal to fully immerse yourself in the beauty of the Eastern Shore, or make your way to spend time in either Annapolis, Baltimore or Washington DC. 

Looking for fun things to do with kids in Baltimore? I have you covered! 

When To Visit

The best time to visit St. Michaels is in the late spring through early fall, particularly from April to October. This period offers mild to warm weather, ideal for outdoor activities such as boating, walking around the town, and enjoying waterfront dining. The summer months are the busiest, but also offer the full range of family-friendly events, festivals, and boat tours. Fall brings cooler temperatures and stunning foliage, adding a different kind of charm to the town.

Areas to Visit on the Way to St. Michaels

St. Michaels is easily accessible by car from major cities like Washington, D.C., Baltimore, and Philadelphia. Along the way, you can make stops at the following family-friendly spots:

• Annapolis, Maryland: Just an hour away from St. Michaels, Annapolis is a great stop for exploring a larger historic town with plenty of history. If you are traveling over the Chesapeake Bay, it’s a great stop on your way! Visit the United States Naval Academy, stroll through the historic downtown area, or take a boat tour of the Severn River.
• Eastern Neck National Wildlife Refuge: Located on the way to St. Michaels, this refuge offers walking trails, opportunities for birdwatching, and the chance to explore the natural beauty of Maryland’s Chesapeake Bay region. It’s a perfect place to stretch your legs and introduce kids to the local wildlife.
• Oxford, Maryland: Just a ferry ride away from St. Michaels, Oxford is another historic waterfront town known for its small-town charm and scenic views. The Oxford-Bellevue Ferry is the oldest privately operated ferry in the U.S. and provides a unique and fun experience for kids and adults alike.

Things to Do with Kids in St. Michaels

• Chesapeake Bay Maritime Museum: A must-visit for families, the Chesapeake Bay Maritime Museum offers hands-on exhibits and interactive learning experiences about the history and culture of the Chesapeake Bay. Kids can climb aboard historic boats, try their hand at knot-tying, and learn about the importance of the Bay’s ecosystem. The museum also features a working shipyard and offers boat-building demonstrations that are fascinating for visitors of all ages. It’s also the venue for many weddings, so be sure to check the hours prior to your trip. 
• Boat Rides and Cruises: No visit to St. Michaels is complete without spending time on the water. Families can enjoy a variety of boat tours, including sailing cruises, historic skipjack rides, or even renting kayaks for a more personal adventure. Patriot Cruises offers a narrated boat tour of the Chesapeake Bay, where kids can learn about the area’s history while spotting wildlife such as ospreys and herons. We’re also big fans of sunset cruises! 
• St. Michaels Nature Trail: This peaceful, 1.3-mile trail is perfect for families looking to stretch their legs and explore the natural beauty of the area. The trail winds through woodlands and along the waterfront, offering a quiet escape and a chance for kids to spot local wildlife. It’s an easy walk that’s great for all ages and is stroller-friendly.
• Explore Talbot Street: Strolling along Talbot Street, the main street in St. Michaels, offers plenty of opportunities for family fun. The street is lined with unique shops, ice cream parlors, and small cafes. Stop for a bite of fresh seafood or grab a sweet treat from one of the local bakeries. Kids will love popping into toy shops or souvenir stores for a special memento from their trip.
• Pickering Creek Audubon Center: A short drive from St. Michaels, the Pickering Creek Audubon Center offers miles of walking trails through woodlands, wetlands, and meadows. It’s a great place for families to enjoy nature while learning about conservation and birdwatching. The center often hosts kid-friendly programs, including guided nature walks and seasonal events.
• St Michaels Winery and Brewery: Over the last few years, wineries and breweries have become a great place to gather and enjoy time with friends, with kids in tow! While they don’t have the largest tasting room to gather, a stop at St. Michaels Winery or Eastern Shore Brewing offers parents a chance to relax while the kids enjoy snacks or explore the nearby area. Both are located in the historic district, and many local eateries offer family-friendly dining in the same area, making it a convenient spot to unwind after a day of exploring.
• Hooper Strait Lighthouse: Located on the grounds of the Chesapeake Bay Maritime Museum, the Hooper Strait Lighthouse is a fully restored screw-pile lighthouse that offers a glimpse into the life of lighthouse keepers. Families can climb to the top for panoramic views of the Bay and learn about the important role lighthouses played in the region’s maritime history.
• Paddleboarding or Kayaking: For families with adventurous kids, taking a cruise on a standup paddleboard or a kayak along the calm waters of the Chesapeake Bay is a fun and memorable experience. There are several local outfitters, like Shore Pedal & Paddle, that rent gear and offer lessons, so even beginners can get out on the water and enjoy the scenic beauty of the Bay.
• St. Michaels Community Center: Check the St. Michaels Community Center schedule for family-friendly events during your visit. The center often hosts fun activities like craft workshops, outdoor movie nights, and seasonal events that are perfect for kids. It’s a great way to experience the town’s local vibe and participate in community activities.
• The Inn At Perry Cabin: This Inn is absolutely beautiful and full of coastal charm. The property is stunning and a lovely place to stay if you are able to get a reservation. 
• Muskrat Park: A beautiful .5-mile walking path along the water, perfect for a leisurely stroll on Saturday mornings. 
• Listen to Live Music: During the season, there are multiple places to catch live music. Especially if you are in the heart of St Michaels, you will be sure to find a restaurant with a musician or a band. 
• Eat! You should be prepared for lots of local culinary delights, especially if you enjoy seafood like steamed blue crabs and oysters. Crabcakes and football! 
• St Michaels Farmers Market: Open April through November, you will find this charming farmers market with goods from local shops, unique gifts, beautiful flower bouquets, and more. 
• Visit Local Coffee Shops: This is one of the first things I look up when I plan our family vacations, where can we stop for a good cup of coffee. Bonus points if it’s Instagram worthy. Check out Rise Up coffee, Blue Heron Coffee and The Blue Crab. 
• St Michaels Museum: A local look at the surrounding area of the Eastern Shore, a view into the historic homes and when they were built and the rick maritime heritage of how St Michaels came to be. 

St. Michaels is a perfect destination for a relaxed family getaway. With its small-town charm, rich history, and plenty of outdoor activities, it offers a balance of fun and educational experiences for families with kids of all ages. Whether you’re exploring maritime history at the museum, spending an afternoon wine tastings, taking a scenic boat ride, or simply enjoying the natural beauty of the Chesapeake Bay, St. Michaels has plenty of things to do for families looking to escape the hustle and bustle and enjoy some quality time together.