A Day Trip Guide to St. Michaels

Over on the Eastern Shore, you’ll find a small, quaint town packed with activities for everyone. Founded more than 350 years ago, St. Michaels is steeped in history, but with plenty of fun for modern visitors. It’s a popular day trip destination right on the Chesapeake Bay that is perfect for families, couples, and even a solo traveler. If you want to get out of your neighborhood and explore somewhere new this summer, add St. Michaels to your list. I’ve got the itinerary recommendations you need, including things to do morning, noon, and night.

How to Get There

St. Michaels is a waterside town accessible by both car and boat. It’s about 50 miles from Annapolis, if Bay Bridge traffic is light, it shouldn’t take more than 90 minutes. By boat, it’s 16.6 nautical miles.

There are many free parking lots around town. Everywhere is walkable; from north to south, the main stretch of Talbot Street is less than two miles. And there are lots of signs pointing tourists to public restrooms.

Boats can dock at one of several marinas including St. Michaels Marina, Harbour Inn, and Higgins Yacht Yard. You can also “drop anchor in the Miles River or St. Michaels harbor and catch the Harbor Shuttle water taxi into town.”

Watermark has several tours that go from Annapolis to St. Michaels, including Day on the Bay, which has a special Father’s Day Cruise. It includes tickets to the Chesapeake Bay Maritime Museum (CBMM) and three hours on-shore before heading back to Annapolis. You can put their cruises for OysterFest (November 2026) and WineFest (April 2027) on your calendar.

Now that you know how to get there, let’s plan your day.

Morning Pick-Me-Up

Don’t start off in a rush. Slow down with a cup of coffee (or something less caffeinated) and a bite to eat. Visit The Blue Crab coffeeshop inside a bright yellow building a block west of Talbot Street. They have nutritious breakfast foods, both savory and sweet, cooked in their own kitchen. After 11 AM they’ll fix you a salad or sandwich. Of course, there’s plenty of pastries available to go with your drink.

Other Options for Food and/or Coffee:

Eat Sprout: Scratch-made, grab-and-go food. Espresso bar and bottled drinks.
Blue Heron Coffee: Drinks only. Pour-over coffee available.
The Galley: Open all day, so it has everything from breakfast to dinner. They serve alcohol, if you want breakfast to include a Bloody Mary.

Out and About

No trip to St. Michaels is complete without a visit to the Chesapeake Bay Maritime Museum. Its sprawling campus has history, nature, and fun both on land and on the water.

Start at the welcome center to buy tickets. On Sundays, all summer, it’s free for kids 17 and under! The welcome center has historical seacrafts to view. And on July 1, their new exhibit Stories from the Shoreline opens. It will give visitors a chance to learn about the people who have lived and worked along these waterways.

Before you venture out onto the campus, grab a map and ask a volunteer for advice on what route you should take. Here are some of the highlights:

Get a Picture with Miss Freedom: Their Emblems of America exhibit will open on Flag Day, but Miss Freedom is always keeping watch.
Learn about hard-won freedom: See the exhibition Bear Me Into Freedom, about Frederick Douglass’ life in Talbot County. Then go back down to the first floor for Sailing to Freedom, to see how the Chesapeake Bay was a vital route along the Underground Railroad.
Then Step Onto a Skipjack: Learn about the importance of oystering on the Chesapeake and how cultures were built on a foundation of oyster shells.
Walk the Shoreline: Look into the grasses for snakes, eels, and more. Then check out their tanks for an up-close look at oysters and crabs. You can see if you can catch these yourself using the same tools and techniques as watermen and women in the past.
Play on the Katie G. and Thor: Workboats brought on land for kids (young and old) to explore and pretend to pilot.
Climb to the Top of Hooper Strait Lighthouse: Annapolitans will recognize the cottage-style lighthouse like our Thomas Point Shoal Lighthouse.
An Afternoon Cruise: Come back after lunch to climb aboard PATRIOT for a 70-minute, narrated historical cruise along the Miles River.
Don’t Forget the Gift Shop: The Chesapeake Bay Maritime Museum has apparel, jewelry, books, toys (so many toys!), and more in their gift shop.

Other Options for Morning Activities:

Historic Walking Tour: St. Michaels Museum offers 90-minute tours each Saturday at 10 AM, May through October. Adults cost $15 and children (under 18) are free.
Playgrounds: There is a small playground with a pirate ship in Hollis Park near the Chesapeake Bay Maritime Museum. When I visited, the pirate ship itself was closed off. There’s a larger playground in Perry Cabin Park, to which you can drive or walk.
Biking: The Oxford/St. Michaels trail is 29.6 miles and ideal for a scenic bike ride. It begins in St. Michaels, ends in Oxford, and includes a ferry ride on the Oxford-Bellevue Ferry. You can rent a bike from Shore Pedal & Paddle.
Kayak/Stand-up Paddleboard: Shore Pedal & Paddle will rent out kayaks and stand-up paddleboards, as well.
Golf: The Links at Perry Cabin is the only golf course in St. Michaels. It’s a very short drive from the town.
Farmers Market: On Saturday mornings, browse the stalls of local vendors. Grab some food to take with you if you’re on your way to the beach.

Lunch Break

The Crab Claw is a popular spot for visitors to St. Michaels. Get a single or a dozen steamed crabs to pick while appreciating the water views. For vegans, they have a Beyond Burger. They only have two options on their children’s menu. However, if your kids are like mine, they’ll be happy with crabs.

Other Options for Lunch:

Corah’s Corner: Indoor and outdoor dining on Talbot Street. The fish ‘n’ chips, salmon BLT, or their flatbreads will make for a perfect lunch.
Ava’s Pizzeria & Wine Bar: They have classic pizza, sandwiches, and “Eastern Shore” beignets.
Gina’s Café: Go there for unique takes on tacos and quesadillas (or ‘dillas’ as they call them), which you can get savory or sweet. Keep in mind, they don’t take reservations, and they prefer that diners pay with only one check.

Shop and Stroll

After a busy morning and a filling lunch, take it easy and do some window shopping…or real shopping. Spend some time in Book Hounds, an adorable independent bookseller where dogs are welcome (of course). Browse the rooms, including the back where little ones can plop down on a mushroom cushion to read awhile. Families should note that every other Saturday morning, the shop will be open early for storytime. Kids can enjoy the story while parents browse before the shop officially opens at 10 AM.

If you’re not too loaded down with books, there’s plenty more shopping to do. For souvenirs and gifts, try The Preppy Redneck or Pemberton Pharmacy & Gifts. But just walking up and down Talbot Street, you’ll see shops that cater to all styles.

Any town that was founded in the 17th century is bound to have some good antiques. The Shops at Sea Captain’s Cottage and Antiques on Talbot are packed with vintage items. If you want something on-theme, grab an oyster plate or a decoy duck.

More to do in the Afternoon:

St. Michaels Museum: Learn about “The Town That Fooled the British.”
Classic Motor Museum: Car-enthusiasts will love this museum, which also provides training for those who want to become automotive service technicians.
Public Library: The library is always a good spot to take a break. The St. Michaels branch of the Talbot County Free Library is over on Fremont Street, away from the busy Talbot Street thoroughfare.
Diana’s Tilton Hilton: More than 100 types of hot sauces. If that’s not enough, they have chocolates, fudge, and “swag.”

Dinner and Dessert

Families with kids will like Sam’s Pizza & Restaurant. Couples looking for a romantic meal can savor Bistro St. Michaels. For something more casual, try San Miguels Mexican Food. And for your girls’ trip, Limoncello is a picturesque spot with sidewalk seating on Talbot Street.

On Thursdays, many restaurants, wineries, and taverns will have special dinners and tastings. Chef’s Table Thursdays in St. Michaels allow proprietors to stretch their culinary muscles with Eastern Shore flavors. Reservations, and multiple visits, strongly encouraged.

If you want to grab a sweet treat (any time of day, not just after dinner), there are ice cream and candy shops around town. Justine’s Ice Cream Parlour has seating inside, perfect for those hot days when you don’t want your cone to melt. There’s also JoJo’s Ice Cream with window service and decadent, farm-fresh flavors. On busy days, both locations are likely to have lines, so pack your patience.

Grab a box of candy for yourself or as a gift. Olde Town Candy Company is a delightful destination with popular candies, toys, and souvenirs. And visit Arnaiz Chocolat for rich, customizable confections.

A Night on the Town

Anyone who is blissfully without kids on their trip to St. Michaels will have plenty of nightlife to enjoy. Head to Carpenter Street Saloon or Foxy’s Harbor Grille for drinks and music. If it’s a Friday or Saturday night and you aren’t ready for the party to be over, Talbot St. Tavern is open until 1 AM.

Sailing Charters: St. Michaels Sailing Charters will take you out on the Lady Patty or the Epiphany. You can have a sunset champagne sail, a beer tasting cruise, or a wine tasting cruise. And, no pressure, they also have a marriage proposal cruise.
Concerts in the Park: Thursdays starting at 6 PM, see live music in Muskrat Park.
Ghost Tours: After sunset, go on a walking ghost tour with Chesapeake Ghosts or US Ghost Adventures…if you dare.

St. Michaels on the Eastern Shore is the low-stress, no-pressure day trip that adults and kids will love. Whether you love the water, the history, or just the pace, this town has so much for you to do. Hop in the car or boat and head over to St. Michaels this summer!