Inn At Perry Cabin

Charming bistro serving classic Italian fare such as pasta, pizzas & risotto, plus wine & spirits.

Casual landmark crab shack offering regional seafood with outdoor tables & views of the Miles River.

Elegant harborside B&B in a historic home with porches, water views & antiques-filled rooms. Set in a circa 1850 shipbuilder's home overlooking St. Michaels Harbor, this elegant B&B is 0.1 miles from the Chesapeake Bay Maritime Museum and 10.2 miles from Easton. Refined, traditional rooms are furnished with antiques, hardwood floors and original artwork, and come with private bathrooms (1 with a Victorian copper tub), cable TV and free Wi-Fi. Features in some rooms include ornamental fireplaces and wall-mounted flat-screen TVs. Most have water views. Full breakfast, and evening sherry and port are complimentary. There's also a porch with rocking chairs.

Charming, old-fashioned ice cream parlor with a huge menu of creative shakes & sundaes.

New American mainstay providing a market-fresh menu with gluten-free options in a romantic setting.

LYON RUM is the flagship product of Windon Distilling, located in Saint Michaels, Maryland, steps from the Chesapeake Bay. Founded in 2012, the distillery launched on 12/7/13 with a signature line of rums paying tribute to the rich, spirited traditions of the Eastern Shore. LYON spirits start with intentionally-sourced raw ingredients, and are truly hand-crafted - mashed, fermented, and double-distilled in small pot stills - every step of the way, resulting in a superior and unique final product. The goal is to create distinctly American spirits - working to define the category of New American Rum, while experimenting with obscure and varied finishes. Every spirit passes through the hands, and discerning palates, of the LYON RUM team.

Chic space with stunning river views serves a seasonal American menu and lovely afternoon tea, perfect for a special occasion or weekend brunch.

Local pub serving hearty American fare in a laid-back setting with a model train, pool & live music.

Hopping riverfront spot with a patio offering seafood eats, local craft beer on tap & live music.

Nestled by the marina, St. Michaels Harbor Inn offers nautical-themed rooms, a spa, and a vibrant outdoor pool, all just a stroll from charming shops and eateries.