Experience Freeport (Sample Itinerary)

Shopping on Freeport's Main StreetDay 1:

  • Arrive at your Freeport B&B for check-in in the afternoon or early evening
  • Walk to L.L. Bean for some quick shopping
  • Walk to restaurant for wonderful dining
  • After dinner browse through other shops before returning to your cozy B&B

Day 2:

  • Drive to Pemaquid Point lighthouse and park
  • On the way back to Freeport, stop in Damariscotta (or Wiscasset, or Boothbay Harbor) for lunch
  • Stop in Boothbay Harbor for local shops, wonderful views, and possibly a whale-watching tour (in season)
  • Return to Freeport allowing plenty of time to get to the L.L. Bean Factory Store (closes at 9 pm), then on to other stores for more shopping (L.L. Bean’s other stores are open 24 hrs)
  • Dinner at another excellent Freeport restaurant
  • Evening shopping in Freeport Village

Day 3:

  • Drive to Portland Head Lighthouse in Fort Williams Park, Cape Elizabeth
  • After enjoying the beauty of the lighthouse and park, continue through Cape Elizabeth to Two Lights State Park, and visit the lighthouses there
  • Enjoy a late lunch or early supper at The Lobster Shack at Two Lights
  • Return to Portland and wander the shops and restaurants in the Old Port.
  • Come back for more evening shopping in Freeport Village

Day 4:

  • Make last-minute plans for any activities before traveling home
  • Make a reservation for your next visit to Freeport!
  • Bid a fond farewell to your hosts!