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Cape Cod Weekend Guide: Beaches, Lobster Rolls, and Small Towns

The perfect three-day Cape Cod itinerary — from Chatham's Main Street to the dunes of Provincetown.

6 min readUpdated August 16, 2026

Cape Cod Weekend Guide: Beaches, Lobster Rolls, and Small Towns

Day 1: Mid-Cape and Chatham

Cross the bridge and head to Chatham for a classic Main Street walk, a visit to the lighthouse, and fried clams for lunch. Settle into your cottage in the afternoon.

Day 2: Outer Cape beaches

  • Morning coffee in Orleans
  • Beach time at Nauset Light or Coast Guard Beach
  • Lunch in Wellfleet
  • Evening drive to Provincetown for dinner and sunset

Day 3: Provincetown and home

Walk Commercial Street, visit the Pilgrim Monument, and grab one last lobster roll before the drive back. Leave early or late to beat bridge traffic.

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