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May 14, 2022
Saint Michaels, MD

Kelly & Jordan

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    Things To Do

Things To Do

St. Michaels is a beautiful and historic harbor town on Maryland's Eastern Shore. There is a ton to do, eat, and drink in town all within walking distance. There are numerous outdoor activities including sailing on historic Skipjacks, kayaking, golfing, and biking. St. Michaels is also known for their food scene offering a range of options in town and on the water. There are a number of boutique shops in town to explore that offer specialty foods, jewelry, clothing, home decor, and art. We hope you explore some of our favorite spots below!

Inn at Perry Cabin

308 Watkins Lane, Saint Michaels, MD 21663
, (410) 745-2200

An upscale spot for sipping cocktails or rare whiskeys on an Adirondack chair by the water! They have a restaurant and spa services on-site as well. You can also inquire about day memberships to play a round of golf at the Links at Perry Cabin.

St. Michaels Farmers Market

206 South Talbot Street, St. Michaels, MD

Check out the local farmer's market - located in the parking lot behind the Pemberton Pharmacy. Open Saturdays 8:30am - 11:30am.

Blue Heron Coffee

500 South Talbot Street, Saint Michaels, MD 21663
, (720) 841-9065

Our favorite spot for locally roasted coffee - we recommend their cold brew!

The Blue Crab

102 South Fremont Street, Saint Michaels, MD 21663
, (410) 745-4155

Coffee shop in town serving breakfast and lunch.

The Galley Restaurant & Bar

305 South Talbot Street, Saint Michaels, MD 21663
, (410) 200-8572

A popular breakfast spot in town.

Carpenter Street Saloon

113 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-5111

The HOTTEST bar in town and open late -- we'll be posting up there Saturday night! Has live music weekend nights and a shuttle to bring you home at the end of the night. Also offers a solid morning-after breakfast ;)

Gina's Cafe

601 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-6400

Our favorite spot for tacos and fresh margs! Menu is pescatarian/vegetarian only - but don't let that stop you, carnivores...

St Michaels Crab & Steak House

305 Mulberry Street, Saint Michaels, MD 21663
, (410) 745-3737

A Rivera family haunt and just next door to Foxy's. Awesome seafood and drinks on the water - though Sam would recommend the pork chop!

Foxy's Harbor Grille

125 Mulberry Street, Saint Michaels, MD 21663
, (410) 745-4340

A fun waterfront restaurant/bar with great food and drinks. Their crushes are exceptional! Live music on Sunday evenings.

Theo's Steaks, Sides & Spirits - St. Michaels

407 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-2106

Kelly and Jordan's "go-to" spot - we even came here for our post-engagement dinner!

Ava's Pizzeria & Wine Bar - St. Michaels

409 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-3081

Wood-fired pizza spot with a great patio!

Bistro St. Michaels

403 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-9111

A delish French bistro - with a great happy hour and Sunday brunch too!

Limoncello Restaurant and Wine Bar

200 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-3111

Tasty Italiano! Try their limoncello martinis!

Eastern Shore Brewing

605 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-8010

Come here for a tasty local brew and to check out some taxidermy...

LYON RUM // Windon Distilling Company

605 South Talbot Street, Saint Michaels, MD 21663
, (443) 333-9181

The local rum distillery in town! A Peter Preston fav...

St. Michaels Winery

609 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-0808

The local winery in town with tastings and a large outdoor patio!

Great Shoals Cellars

500 South Talbot Street, Saint Michaels, MD 21663
, (443) 786-0965

No thirst goes unquenched in this town - this is another wine tasting room...with hard ciders too!

Chesapeake Bay Maritime Museum

213 North Talbot Street, Saint Michaels, MD 21663
, (410) 745-2916

For you history buffs, this museum in town is dedicated to preserving and exploring the history, environment, and culture of the entire Chesapeake Bay region. Has awesome waterfront grounds with various exhibits to explore and historical skipjacks docked!

Classic Motor Museum of St. Michaels

102 East Marengo Street, Saint Michaels, MD 21663
, (410) 745-8979

Check out 'Cars and Coffee' on Saturdays 9am-11am!

Patriot Cruises

213 North Talbot Street, Saint Michaels, MD 21663
, (410) 745-3100

For those who like a little more brackish spray with their history, this is a narrated historic cruise through the scenic waters surrounding St. Michael's. Recommend booking tickets in advance!

Sail Selina II

101 North Harbor Road, Saint Michaels, MD 21663
, (410) 726-9400

Prefer sailing and champagne? Offers numerous charter options (up to six people) aboard the luxury sailing yacht Selina II.

Shore Pedal & Paddle

500 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-2320

Offers kayak, paddleboard, and bike rentals.

TriCycle and Run

929 South Talbot Street, Saint Michaels, MD 21663
, (410) 745-2836

Another bike rental spot slightly outside of town.

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