TO EAT • TO DRINK • TO BUY • TO DO

  1. SNOWY OWL 2624 Main Street, Brewster (Coffee, tea, baked treats)
  2. CAFÉ ALFRESCO 1097 Main Street, Brewster (Breakfast and sandwiches)
  3. HOLE IN ONE 98 Cranberry Highway, Orleans (Breakfast, lunch, bakery)
  4. EAT CAKE FOR BREAKFAST 26 Wampum Drive, Brewster (Bakery)
  5. HOT CHOCOLATE SPARROW 5 Old Colony Way, Orleans (Chocolate, coffee, desserts, fudge)
  6. COBIE’S 3260 Main Street, Brewster (Clam shack and ice cream)
  7. JT’S SEAFOOD 2689 Main Street, Brewster (Casual seafood and ice cream)
  8. CHILLINGSWORTH 2449 Main Street, Brewster (High-end spot with classic French cuisine)
  9. BREWSTER FISH HOUSE 2208 Main Street (Contemporary bistro-style menu)
  10. KATE’S SEAFOOD 284 Paine’s Creek Road (Casual seafood and Ice cream)
  11. SESUIT HARBOR CAFÉ 357 Sesuit Neck Road, Dennis (Seafood shack & raw bar on the water)
  12. GUAPO’S TORTILLA SHACK 239 Underpass Road, Brewster (Baja-Mexican beach shack)
  13. STONE L’OVEN PIZZA 280 Underpass Road, Brewster (Casual brick-oven pizza)
  14. THE BREWSTER SCOOP 1929 Main Street, Brewster (Ice cream)
  15. OCEAN EDGE BEACH BAR 2907 Main Street, Brewster (Cocktails overlooking the bay)
  16. THE WOODSHED 1993 Main Street, Brewster (Local watering hole with live music)
  17. LOST DOG PUB 63 Route 6A, Orleans (Happy hour food and great cocktails)
  18. THE BEACHCOMBER 1120 Calhoon Hollow Road, Wellfleet (Beach bar with live music)
  19. FRIEND’S MARKETPLACE 57 Main Street, Orleans (Market, outdoor garden center)
  20. SHAW’S 9 West Road, Orleans (Chain grocery store with delivery via Instacart)
  21. THE BREWSTER STORE 1935 Main Street, Brewster (Old fashioned general store)
  22. THE BREWSTER BOOK STORE 2648 Main Street Brewster (Books, gifts)
  23. CHATHAM BARS INN FARM 3034 Main Street, Brewster (Farm stand, farm-to-table dinners)
  24. COTTAGE 403 S. Orleans Road #8, South Orleans (Art, vintage apparel, home goods)
  25. HANDCRAFT HOUSE 3966 Main Street, Brewster (Art & fine gift gallery)
  26. ARTIST COTTAGES 15 Old Colony Way, Orleans (Cape Cod artists selling unique art)
  27. CROSBY LANDING BEACH 276 Crosby Lane, Brewster (Closest bay beach)
  28. NICKERSON STATE PARK 3488 Main Street, Brewster (Park with 8 freshwater ponds)
  29. CAPE COD RAIL TRAIL 3488 Main Street, Brewster (25-mile bike path)
  30. PAINE’S CREEK BEACH 526 Paine’s Creek Road, Brewster (Bay beach with stunning sunsets)
  31. SPARKY’S HAYRIDES Kate’s Seafood, Brewster (Sunset hayride to Paine’s Creek beach)
  32. CAPE COD MUSEUM OF NATURAL HISTORY 869 Main Street, Brewster (Museum)
  33. RAIL TRAIL BIKE & KAYAK SHOP 302 Underpass Road, Brewster (Bike + kayak rentals)
  34. NAUSET BEACH 250 Beach Road, Orleans (Ocean beach with parking lot and snack shack)
  35. ART’S DUNE TOURS 4 Standish Street, Provincetown (Off-road tour of Provincetown dunes)
  36. SUPFARI ADVENTURES Brewster and Orleans (SUP + kayak rentals/tours)
  37. WELLFLEET DRIVE-IN 51 State Highway Route 6, Wellfleet (Drive-In Movie + Flea Market)
  38. DOLPHIN WHALE WATCH 307 Commercial Street #1, Provincetown (Whale watching tour)
  39. THE ALLEY BOWLING + BBQ 191 MA-6A, Orleans (Bowling alley + bar/BBQ restaurant)