A Weekend in St. Michaels, MD

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Advisor - Elisabeth McCabe
Curated By

Elisabeth McCabe

  • Maryland

  • Food & Wine

  • Road Trip Travel

  • Luxury Travel

  • History

  • Long Weekend

  • Sightseeing

Discover the 1879 Hooper Strait Lighthouse.
Curator’s statement

St. Michaels is a quaint and historical waterfront town on the Eastern Shore of Maryland. An easy road trip from DC, Baltimore, Philadelphia and NJ yet worlds away. Also known as the "town who fooled the British", charming St. Michaels offers a plethora of activities for a wonderful weekend getaway. You might recognize St. Michaels from the movie Wedding Crashers, which was filmed at the Inn at Perry Cabin and surrounding areas.

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Where to stay in St. Michaels, MD

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Things to do in St. Michaels, MD

Boats docked at Perry Cabin can be used for day and sunset cruises.

The Inn at Perry Cabin has a plethora of activities included in the resort fee both on and off the water. From Perry Cabin's dock, you can take out a kayak or paddle board and explore the harbor or coves along the river. They also have an impressive fleet of boats and sailboats that are available for day and sunset cruises. Don't miss the beautiful spa for one of the best massages. During the warmer months, an infinity edge pool with poolside food and drink service provides a break from the heat. For those wanting to be active, there is a well equipped gym and three Har-Tru tennis courts. Additionally, just down the road is the stunning golf course, The Links at Perry Cabin, designed by Pete Dye. Finally, the resort offers many activities such as bingo, painting, and a daily champagne toast.

Just next door to the hotel is the Chesapeake Bay Maritime Museum, a waterfront, interactive museum set on 18 acres. Since its opening in 1965, the museum has told the stories of people from the entire Chesapeake region. The museum also showcases the connection between boating and the oyster, fishing and crabbing industry. This museum is very interactive and lets you explore old boats, a lighthouse from 1879 and even rake for oysters.

Patriot Cruises, a 65-70 minute narrated historical cruise, is another favorite activity. The ride down the Miles River is extremely scenic and full of information on the surrounding area.

The town's main drag, South Talbot Street is full of charming shops and restaurants. Don't miss the American Holiday.

Just off the main shopping area are several places for tasting some local spirits. Eastern Shore Brewing Company offers their flagship St. Michaels Amber Ale along with a variety of year-round and seasonal offerings. St. Michaels Winery has a tasting room where you can sample their whites, reds and rose wines. Finally, don't miss the Lyon Rum Distillery. Lyon Rums are double distilled in small, traditional pot stills in Saint Michaels using 100% Louisiana sugarcane, making for a truly American Rum.

Places to eat & drink in St. Michaels, MD

Steamed crabs at The Crab Claw.

Stars at Inn at Perry Cabin: Included as a perk for free breakfast for two when booking through Fora. Also great for lunch or dinner. Upscale dining, highlighting regional specialties.

The Galley: A great place to grab breakfast or lunch. Food is always excellent and you can't beat their bloody marys.

Avas: A consistently solid spot for brick oven pizza. The "Chef's Favorite" is incredible.

The Crab Claw: A St. Michaels institution since 1965, open March - October. This is the go-to place for fresh steamed crabs. Get cracking!

Theo's Steaks, Sides & Spirits: Steakhouse with New Orleans-inspired fare in a 100-year-old historic home.

Limoncello: Quaint spot offering authentic Italian cuisine for lunch and dinner.

The Blue Crab Coffee: A cute coffee shop in town.

Justines: The BEST ice cream!

Advisor - Elisabeth McCabe

Travel Advisor

Elisabeth McCabe

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Looking for more travel inspiration? Check out Jessica Rausch's guide, Local's Guide to History & Food in Annapolis, MD.

This guide is part of our ongoing series on travel to Maryland.