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Visit Historic St. Michaels

By / Photography By Liz Lind & Kurt Jacobson | June 08, 2017
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Liz Lind watercolor of St. Michaels
Watercolor of St. Michaels Chesapeake Maritime Museum by Liz Lind.

It’s easy to see why people fall in love with this bustling, walkable, fun gem on Maryland’s Eastern Shore. Take the time for your own summer getaway and see what all the excitement is about.


St. Michaels has long been known for its history and waterfront charm. It is one of the most charming towns in Maryland, with a list of things to do, eat, drink and visit just right for a short summer escape. While visitors from Baltimore, DC, and even New York City invade the town on summer weekends for food, fun, and drink, all this love and attention can create traffic jams and long waits. To beat the crowds, consider a mid-week visit. The town is still in its full glory, restaurants and lodging choices have something for most any budget, and the museums, shops, sail boat trips, kayaking, paddle boarding, bicycling, and more are waiting to craft a perfect visit.

The first task is to decide where to stay. For a something-to-remember getaway, the Sail St. Michaels package at The Inn at Perry Cabin are $700 and up, with options including a luxury water-view suite with a private outdoor terrace – the perfect spot for a full breakfast spread to start the day. A two-hour sailing trip on one of the Inn’s Alerion Yachts comes with this package, and seeing the scenic Chesapeake Bay on one of the Inn's gleaming sailboats on a sunset cruise is the ultimate way to finish your day.

For more indulgence, The Inn at Perry Cabin is also home to the Linden Spa, where a couple’s massage can be arranged seven days a week. The onsite Stars restaurant is overseen by Chef Ken MacDonald, who uses locally-sourced ingredients including many right from the Inn’s gardens. They have hired an enthusiastic farm manager, Phal Mantha, to supply the kitchen with organic, home-grown produce from the resort’s grounds.

Another lodging option is the Five Gables Inn and Spa on Talbot Street, which puts you within walking distance to most everything in St. Michaels. At Five Gables, rooms are located in one of three historic homes on the property. Prices range from $195 to $345 a day, and all rooms include access to an upscale continental breakfast, indoor pool, steam room, sauna, and bicycles. Although children under 12 are not allowed, they do feature four rooms and one suite that are dog friendly.

St. Michaels is one of the most dog friendly towns you will find anywhere. Several restaurants invite owners and their well-behaved dogs to dine alfresco, and most of the dog-friendly establishments have bowls of water and dog biscuits for Fido. One of the most popular is St. Michaels Crab and Steak House. Take a seat outside and mingle with watermen, townsfolk, and other visitors while the ebb and flow of bayside life draws you in. The menu is full of seafood options and, of course, steak. Try the crab balls appetizer to start, choosing the broiled-not-fried option, and pair it with glass of Prosecco or St. Michaels ale on tap. The broiled seafood platter has a crab cake, flounder, shrimp and scallops cooked in lemon and wine. All entrees come with two sides making sure you don’t walk away hungry!

On Talbot Street, the main thoroughfare in town, try Bistro St. Michaels, Limoncello Italian Restaurant and Wine Bar, or 208, a fine dining establishment. Limoncello is where you’ll find the delicious Cinghiale (wild boar) on house-made pappardelle. The owner is from Tuscany, Italy, making this the real-deal Italian restaurant to consider. Ava’s Pizzeria and Wine Bar is where you’ll find award winning handmade pizzas. At Ava’s they make their own dough and mozzarella each day and serve 17 wines by-the-glass at a very affordable price. And if you’re looking for a great breakfast spot, try Crepes by the Bay for fresh made crepes in a laid-back setting.

St. Michaels is home to water adventures of all kinds – from sailing trips to kayak exploring. Sail Selina ll offers luxury sailing yacht trips for up to six people, including sunset champagne, dinner sails, beer tasting cruises, moonlight sails, or whatever inspires you! If you want to provide your own muscle power on the water, Shore Pedal & Paddle rents paddle boats and kayaks, and also offers lessons if you want to learn the art of paddle boarding.

For history buffs, the Chesapeake Bay Maritime Museum is a must. This multi-faceted museum has a floating fleet of historic boats, 12 exhibition buildings, and changing exhibits that tell the story of crabbing, oyster catching, and life on the bay. They also have row boats and sail boats for rent to create your own history. In town, the St. Michaels Museum at historic St. Mary’s Square shows what a typical waterman’s home looked like in the 1860s in the Sewell House. The Chaney home was built circa 1850 by three free African American brothers, and offers a fascinating view of life in St. Michaels. If cars are your thing, the St. Michaels Classic Motor Museum is the new kid in town. Several classic cars, including the 1920 Buick that was one of the first cars to cross the Bay Bridge in 1952, are on display.

A visit to St. Michaels wouldn’t be complete with a trip to the Lyon Distillery, said to be the first craft distillery in Maryland. They make a dark rum and an overproof rum that are worth stopping by to taste. Your tasting tour should also include the St. Michaels Winery. Grab a chilled glass of their Sauvignon Blanc, best taken outdoors under the shade trees of their patio. A visiting couple also sipping wine shared that they come to St. Michaels about once a month and “are considering a move here.” We totally understand why.

Learn more at stmichaelsmd.org

Photo 1: Sailing the Chesapeake on the Selina II.
Photo 2: Dog-friendly options include Gina’s Cafe.
Photo 3: Bustling Talbot Street.
Photo 4: Outdoor dining is a must while visiting.
Photo 1: Sign at Lyon Distillery.
Photo 2: Patio view at the Inn at Perry Cabin.


Five Gables Inn and Spa
209 N. Talbot Street

The Inn at Perry Cabin
308 Watkins Lane


Chesapeake Bay Maritime Museum
213 N. Talbot Street

Classic Motor Museum
102 E. Marengo Street

Sail Selina ll
101 N. Harbor Road

Shore Pedal & Paddle
500 S. Talbot Street

St. Michaels Museum
201 E. Chestnut Street


208 N. Talbot Street

Ava’s Pizzeria and Wine Bar
409 S. Talbot Street

Bistro St. Michaels
403 S. Talbot Street

Crepes by the Bay
413 S. Talbot Street

Limoncello Italian Restaurant and Wine Bar
200 S. Talbot Street

Lyon Distillery
605 S. Talbot Street

St. Michaels Crab and Steak House
305 Mulberry Street

St. Michaels Winery
609 S. Talbot Street

Learn more at stmichaelsmd.org

Article from Edible Delmarva at http://edibledelmarva.ediblecommunities.com/things-do/visit-historic-st-michaels
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