Maine Vacation Plan, Itineraries for the Freeport Area

There is so much to do in and around Freeport! To help with planning, we have prepared several sample itineraries, based on length of stay and areas of interest, complete with maps and driving directions, for use by guests staying at Brewster House. We also have some articles on one day visits or two day visits to Freeport and the activities you can take in (as well as the one's you may not have time to visit), or special interest sightseeing, like our blog post, "5 Maine Lighthouses You Can Visit (within about an hour of Freeport)", or our article with lighthouse map, "Maine Lighthouses - An Accessible Treasure".

We also have a multi-part guide to visiting all of Maine's regions, entitled "Visit Maine Like A Mainer".

Here is a sample for a four day, three night stay, combining some Freeport shopping with visits to area lighthouses:

Day 1:

  • Arrive at Brewster House for check-in in the afternoon or early evening, request dinner reservations at one of our local restaurants
  • Walk to L.L. Bean for some quick shopping
  • Walk to restaurant for wonderful dining
  • After dinner walk through other shops on the way back to Brewster House


Day 2:

  • Delicious breakfast at Brewster House, make dinner reservations if needed
  • 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 and park at Brewster House, 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 before returning to Brewster House


Day 3:

  • Another good breakfast at Brewster House
  • 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 before returning to Brewster House


Day 4:

  • Enjoy your last breakfast at Brewster House for this visit
  • Make last-minute plans for any activities before traveling home
  • Make a reservation for your next visit to Brewster House!
  • Bid a fond farewell to your hosts!