Reserve a window-side table at the Red Inn, an upscale lodge with a huge brick fireplace and rustic wood detailing. Fresh seafood like oysters and cod are the specialties, all caught off the Cape Cod shores. Start with a pre-dinner tea-infused martini ($10) on the deck, where you can watch the evening sun glinting across the boats.
Assemble a picnic lunch at Far Land Provisions, a café and country grocery that sources its produce and meats from regional farms. Order the best-selling Pilgrim Lake sandwich—turkey, Cheddar, and cranberry mayo piled atop a bulky Portuguese roll ($6.50)—along with a homemade chocolate-chip cookie.
Feast on New England staples at the Mayflower Cafe, a local stalwart with vinyl booths, wagon-wheel lamps, and walls covered with caricatures from the forties and fifties. The spot is known for the best Cape-sourced lobster rolls in town: cut chunky and served on a buttered hot-dog bun with shredded lettuce ($13.95).