Where to Eat and Stay in St. Michaels, Maryland

The charming vintage port of St. Michaels is a popular tourist destination and features manicured colonial, federal, and Victorian homes, stunning churches, and a scenic shopping area. Seafood lovers can eat their fill of local crab, fish, and oysters, and those looking to stay the night will find a selection of exclusive inns, bed-and-breakfasts, as well as a lavish resort.

Maryland’s Eastern Shore and Atlantic Beaches

Places to Eat in St. Michaels


Good food with a romantic atmosphere and modern ambience can be found at Theo’s Steaks, Sides, and Spirits (407 S. Talbot St., 410/745-2106, Wed.-Sun. for dinner at 5pm, $13-54) on Talbot Street. This popular eatery offers a small but diverse menu of pub fare and steaks, expertly prepared and presented. Don’t let the paper on the table fool you (it is recycled and they use it instead of linen for “green” reasons), the chef here is an expert with a long culinary résumé and his experience shows.


Theo’s sister restaurant, Ava’s Pizzeria and Wine Bar (409 S. Talbot St., 410/745-3082, daily 11:30am-9:30pm, $8-22) serves exceptional pizza, pasta, and sandwiches. They also have an extensive wine and beer menu. The atmosphere is fun and inviting with an outdoor patio, fireplaces, and even a waterfall. They do not take reservations, but they have a call-ahead list. They are known for pizza, but the meatballs are out of this world.

Picnic tables at The Chesapeake Bay Maritime Museum, located in St. Michaels, Maryland. © Georgesheldon, Dreamstime.


Feeling funky? Then try Gina’s (601 Talbot St., 410/745-6400, Wed.-Sun. noon-10pm, $11-28). This tiny, 1,000-square-foot southwestern eatery on the corner of Talbot Street and East Chew is barely large enough to be termed a restaurant, but they serve up savory, south of the border goodness with a balance of fresh seafood. They have fantastic salsa, fish tacos, drinks, and house-made tortilla chips, in addition to a host of other unique favorites. The staff is super friendly. This is the place to come when your taste buds need a break from the usual restaurant fare. Try the soft shell tacos with crab and guacamole or the crab nachos.

Ice Cream

Mouthwatering ice cream in a friendly atmosphere can be found at Justine’s Ice Cream Parlour (106 N. Talbot St., 410/745-0404, Sun.-Thurs. 11am-8pm, Fri.-Sat. 11am-10pm, under $10) on North Talbot Street. They serve ice cream, floats, shakes, and malts.

Where to Stay in St. Michaels

Accommodations from $100-200

There is no shortage of comfortable bed-and-breakfasts and inns in St. Michaels. The Cherry Street Inn (103 Cherry St., 410/745-6309, $155-180) is one good option, with its convenient location, great breakfasts, and friendly, down-to-earth hosts. Just a short walk from the downtown area, the 1880s Victorian inn offers two suites with queen beds and private bathrooms. The inn was built by a steamboat captain and has been fully renovated.

Bring your kayak or fishing rod to the Point Breeze Bed and Breakfast (704 Riverview Ter., 410/745-9563, $175, minimum stays may be required). This lovely home has 400 feet of waterfront on the harbor, a pier, and complimentary kayaks, canoes, and bicycles for guest use. There are several guest rooms, all decorated with family heirlooms from five generations. Breakfast is included with each stay.

An additional nice bed-and-breakfast option is the Snuggery Bed and Breakfast (203 Cherry St., 410/745-2800, $150-250), with two guest rooms in the oldest residence in St. Michaels.

St. Michaels Harbour Inn Marina & Spa, Maryland. © Jon Bilous, Dreamstime.

Accommodations from $200-300

Also located on Cherry Street is the Dr. Dodson House Bed and Breakfast (200 Cherry St., 410/745-3691, $250-275). This charming bed-and-breakfast is steps from Talbot Street and a stone’s throw from the harbor. The inn was built in 1799 for use as a tavern and also served as the first post office in town. The home still has many of its original features, such as the original fireplaces, woodwork, doors, and glass. It is considered to be one of the best-preserved examples of federal architecture in St. Michaels. The interior is modern but keeps with the character of its time. There are three guest rooms: two with queen beds and one with a king or two twins. All have fireplaces (either wood-burning or electric) and private bathrooms. There are large sofas on the first floor and a second-floor porch for guests to relax on. A wonderful breakfast is served each morning in the elegant dining area.

The St. Michaels Harbour Inn Marina & Spa (101 N. Harbor Rd., 410/745-9001, $209-399) is also on the Miles River. It has 46 guest rooms and a full-service marina. This is a lovely property, but the service can be spotty.

Accommodations over $300

The lavish Inn at Perry Cabin (308 Watkins Ln., 410/745-2200, $365-610) is a grand old resort and spa owned by Orient Express and formerly owned by Sir Bernard and Lady Laura Ashley. It sits on the Miles River and has nice views of the water. The hotel was built around 1816 and is surrounded by antique gardens from the same period. Docking facilities (free for guest use), a fitness center, heated outdoor pool, and complimentary bicycles are part of the property amenities. There are 78 guest rooms. Ask for a room on an upper floor with a view of the water.

Michaela Riva Gaaserud

About the Author

Michaela Riva Gaaserud is a native Virginian and longtime resident of the Washington DC area. Some of her earliest memories are of playing travel guide to visiting relatives as they went to the museums and monuments in Washington DC. Inspired by the enthusiasm she witnessed from first-timers to the city, Michaela began looking for hidden secrets to share with her audience. A particularly inspiring school field trip to the underground depths of the Lincoln Memorial sealed her love for discovering and sharing the marvels of her own backyard.

Michaela has published travel guides on various aspects of the Washington DC region, and her articles have appeared in newspapers, magazines, and international publications such as Canoe & Kayak Magazine and Paddler Magazine. She is also a founding partner at Rainmaker Publishing and an executive producer at Eddyline Media.

Learn more about this author

Pin it for Later