Start from 66 curated places around Cape Cod, MA, then choose the recommendations that fit your guests.
Restaurants & cafés
The Glass Onion
A serious New American dining room in a 1926 building in downtown Falmouth that has been the Upper Cape's go-to grown-up dinner for years. The kitchen leans on local seafood without turning into a fried-clam shack, and the room stays just shy of formal.
Anejo Mexican Bistro & Tequila Bar
A Main Street Falmouth bistro that does fresh, modern Mexican and a deep tequila and mezcal list, guacamole made at the table, and a patio under a big beech tree. It has been a fixture since 2010 and is where Upper Cape locals go when they want something other than seafood.
Trails & outdoors
Great Island Trail
The hardest hike on the Outer Cape: a roughly 5 to 8 mile out-and-back through deep soft sand from Wellfleet's Griffin Island out along a wooded spit to the old tavern site and, if the tide allows, Jeremy Point. Bay, marsh, dunes, and pitch pine, with very few people once you are past the first beach.
Atlantic White Cedar Swamp Trail
A short, easy 1.2-mile loop in South Wellfleet that drops on a boardwalk into a dim, cool Atlantic white cedar swamp, one of the strangest forest pockets on the Cape. Flat, family-friendly, and a complete change of scene from beach and dune in well under an hour.
Things to do
Wellfleet Drive-In Theatre
The last operating drive-in on Cape Cod, a 1957 Route 6 relic that still shows first-run double features on a 100-foot screen all summer, with a snack bar, mini golf, and a playground out front. Pure outdoor nostalgia and the obvious family night when the weather turns clear.
Payomet Performing Arts Center
A nonprofit performing-arts tent on National Seashore land in North Truro presenting music, theater, comedy, and a professional circus over the summer. It is intimate enough that every seat is close, and the circus-by-the-sea programming makes it a rare evening venue that also works for kids.
Landmarks & sights
Pilgrim Monument and Provincetown Museum
A 252-foot granite tower on the hill above Provincetown marking where the Mayflower Pilgrims first landed in 1620, before they moved on to Plymouth. You climb it on a ramp-and-stair switchback, not an elevator, and the top gives you the whole curl of the Outer Cape with the museum at the base covering pirates, the art colony, and town history.
Heritage Museums & Gardens
A 100-acre estate in Sandwich that mixes formal gardens, a working 1908 carousel, and a barn full of antique American cars including a 1930 Duesenberg. The rhododendron and daylily plantings are the reason locals come back across the season, and the grounds are big enough that kids can run while adults wander the collections.