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Grab lunch at local favorite Ava’s Pizzeria & Wine Bar, where you’ll find wood-fired pizzas as well as a special menu for your four-legged companion — the dog menu includes items like beef stew and an organic chicken breast in rice and light gravy. Overall, the town is very dog friendly.
Walk back through town and take your pick of ways to while away an afternoon. Get boozy with a stop at the St. Michaels Winery, which offers by-the-bottle, glass and tasting selections of a variety of Maryland-grown wines, or Eastern Shore Brewing next door, operated out of a historic mill. Prefer something harder still? Lyon Distilling Company makes small batch run and whiskey.
For drinks and dinner, pick your choice of fancy or fun. At Inn at Perry Cabin, there’s the gorgeous view at Stars, serving up American classics with a seafood-focused vibe (get the crabcakes). We love the 208 Talbot with its simply prepared steak and seafood menu, the Hunter’s Tavern at the nearby Tidewater Inn, featuring a local menu of finely-prepared American classics like soft shell crab tempura and Chesapeake gumbo. Or try the always-popular Scossa Restaurant & Lounge, which serves up Italian fare in a lounge-like setting.
Stop for lunch at The Crab Claw Restaurant in Easton, one of Maryland’s most famous crab houses. Learn how to crack a crab and the difference between a male and a female. A male, known as a “Jimmy,” has a long inverted “T” on its stomach, while a female, called a “Sook,” has a more bell-shaped marking. Although they are known as Blue Crabs, females have red-tipped claws and males have blue ones.