Bring a water bowl and ask for extra deli meat for your pooch at Something Natural (50 Cliff Rd., 508-228-0504), an eatery serving heaping sandwiches on homemade bread and chewy, oversize cookies. Full portions will feed two, and the liverwurst and onion—get it on pumpernickel, with plenty of mustard—is a must (half, $4.95; full, $8.50). There’s a shaded picnic area for noshing with your pet, and Steps Beach is a short walk across the road.
Make a pit stop at Bartlett’s Farm for edible provisions like olives, cheeses, and pâtés before backtracking to Cisco Brewers, a combination brewery, distillery, and vineyard. Three separate outdoor buildings offer tastings and full-size portions of pale ales, artisanal gin, and small-batch Pinots. In the center, there’s a biergarten-like courtyard where dogs run free, and you can eat and try Notch, a single malt whiskey made from beer and barrel-aged for eight years ($44 for a 1.5-oz. sample, including glass).
Taste LOLA 41’s best seller—the caramelized onion and Wisconsin cheddar topped Black Angus sirloin patty ($14.95)—at spinoff Lola Burger, a Broad Street take-out joint that also serves an excellent traditional lobster roll ($19.95). Find a seat on the Front Street benches or eat at the docks to watch the ferry crowds roll in.