Rest
When in a sea captains' town, stay in a sea captain's home. The
Captain Freeman Inn (15 Breakwater Road, 508-896-7481 or 800-843-4664, captainfreemaninn.com, $165-$235 through October) sits right behind the Brewster Store and just up the street from Breakwater Beach. Guests can borrow beach chairs -- or a bicycle for exploring farther afield.
The Isaiah Clark House (1187 Main St., 508-896-2223 or 800-822-4001, isaiahclark.com, $165-$175) has unusually spacious rooms for a circa-1790 structure, permitting queen and king beds and, in some cases, fireplaces. It's a short walk to Kate's Seafood, and not much farther down the road to Paine's Creek Beach, the best of the saltwater swimming holes.
Party
Maybe it's because the town was named after one of the Pilgrim fathers, but Brewster's idea of summer nightlife is hanging out at the beach to watch the afterglow of sunset. Should you get thirsty, the brews stir at the
Woodshed Lounge (1993 Main St., 508-896-7771) at the Brewster Inn & Chowder House. The pub is also sponsoring a 5.2-mile "Brew Run" on Saturday to benefit Brewster Rescue and Safety.
Through Aug. 25, the Cape Cod Repertory Theatre (3379 Route 6A, 508-896-1888, caperep.org) is performing the Atlantic City-based musical "Steel Pier" in the Arts and Crafts-style main theater. Cape Rep also has children's performances on Tuesdays and Wednesdays at 10 a.m. through Aug. 22.
Fuel
Dining on Cape Cod doesn't get more haute than the table d'hôte at
Chillingsworth (2449 Main St., 508-896-3640, chillingsworth.com, seven-course menu $59.50-$70, bistro entrees $17-$28). In addition to fine dining, Chillingsworth also offers a more casual a la carte menu in the bistro. Reserve far ahead.
On the other hand, seating is first-come, first-serve at the intimate Brewster Fish House (2208 Main St., 508-896-7867, entrees $18-$29). The sophisticated, contemporary menu makes the best of the local catch (hand-lined fluke, dayboat scallops, local oysters). Go early or late to get seats.
For a more casual approach to seafood, Bayside Seafood and Market (2740 Main St., 508-896-5367, baysideseafoodandmarket.com, lobster rolls $18-$22, clambake $34 per person) steams clams and lobsters to eat on the premises or to take to the beach. The shop also serves baked goods at breakfast and deli sandwiches and panini for lunch.