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Itineraries

Maine Coast Vacation Ideas from Our Freeport Bed & Breakfast Inn

There is so much to do in and around Freeport! To help with planning, we have prepared several sample itineraries with Maine coast vacation ideas, 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 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”

Maine Coast Vacation Ideas

4 Day Maine Coast Stay

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!

Read on for more Maine Coast vacation ideas for shorter visits.

2 Day Freeport, Maine Stay

Day 1

If there is any way to arrive early in the day, this will greatly help to make the most of such a short visit to Freeport. Once you’ve checked in at your cozy B&B, you can stroll into Freeport Village, enjoying the shopping at over 160 shops and a meal at one of the fine restaurants in the village. Of course there’s the L.L. Bean campus, where the factory store is open until 10 p.m. every day but Christmas, and the other L.L. Bean stores never close.

When you run out of steam, stroll back up Main Street, packages in hand, and collapse into a comfortable bed at your Freeport B&B.

Day 2

Today there are choices to make. What should we try to do, and what shall we opt to leave for a return visit?

If you enjoy the magnificent coastal scenery, and the Maine lighthouses (there are over 60 of ‘em), we will definitely have time to visit one or two. We can start to the south, heading into Portland’s Old Port district, browsing among the shops before parking near the Maine State Pier, where we can take a two hour cruise on an antique schooner, built in Maine nearly 100 years ago, at Portland Schooner Co. One of the highlights of the cruise is seeing picturesque Portland Head Lighthouse from the water!

After the cruise, you can drive through the nearby community of Cape Elizabeth with its magnificent (mostly) old homes, to Fort Williams Park, where you can see Portland Head Lighthouse from the landward side, as well as exploring the park, its fort and other amenities.

From Fort Williams Park, continue down the road (to the south – away from Portland) to the road to Two Lights State Park. Here you’ll find “Two Lights” or the Cape Elizabeth lighthouse. Two lights set about 1/4 mile apart, when aligned would give mariners a clear idea of their position. Next to the parking area (up on the hill) is a lobster shack with a wonderful view of the sea (and good food, too).

If there is still time for more, before returning to Freeport, you might travel farther south, stopping at the quaint little town of Kennebunkport, before heading farther south to “the Yorks” (York, York Beach…) and Cape Neddick Lighthouse (also known as “the Nubble” for the small rock island it is on).

Before heading back to Freeport, stop for a light dinner at the Maine Diner in Wells, stop at one of Portland’s many fine restaurants (an amazing number of fine restaurants for the size of the town), or return to Freeport for dinner at another local eatery.

Day 3

Sadly, this is the day to check out (after a wonderful B&B breakfast, of course!).

If time permits, visit the Freeport harbor or Wolfe Neck State Park, for wonderful views of Casco Bay on your way out. Time has run out for the many other things that can easily be done when your trip is based in Freeport. Things like a tour of Eagle Island (Admiral Peary’s home), visits to beautiful Reid State Park or Popham Beach State Park, antique shopping from Bath to Bar Harbor, searching for photo opportunities of moose, and visiting seaside lobster shacks will all have to wait for another visit.

See you again soon!

1 Day Trip to Freeport, Maine

People visiting Freeport for the first time often stay only one night, not realizing how much there is to do in the area. That makes it a bit of a challenge when they ask what they should see in the short amount of time they can spend.

So, what should someone see if they have only a day?

To begin, let’s set some priorities. Do you want to shop? Do you want to see the coast? Visit lighthouses? Farms? Bird sanctuaries? Hike? Sail? Kayak? OK, now we can begin.

For the shopper, Freeport offers the L.L. Bean flagship store (open 24×7!) along with its Bike, Boating and Ski store, Hunting and Fishing Store and, of course, the Outlet. The Outlet is the only one not open 24×7 – its hours are 8 a.m. to 10 p.m. every day but Christmas. There are also over 160 other shops and restaurants, almost all within a few blocks of us, so it is a nice walk.

If you enjoy hiking or the coastal scenery, you have choices, as you will not have time for more than one or two places to visit. Wolfe Neck State Park and Winslow Park are both within the Freeport area. Both are on the shores of Casco Bay and offer wonderful views of the bay, and Wolfe Neck offers hiking trails through the woods and along the shore. Another choice is to visit either Popham Beach State Park or Reid State Park, both offering sandy beaches, magnificent coastal views and views of the offshore islands, as well as hiking trails. Both Popham Beach and Reid are within an easy drive of Freeport.

For hiking of a more inland variety, there is nearby Bradbury Mountain State Park. Not difficult to hike, but somewhat more hilly than the others, Bradbury Mountain is only a few miles from Freeport.

If getting out on the water is your preferred way to see the coast, you have lots of choices. From the wharf in South Freeport you can rent a kayak and take the self-propelled route. Or, take a tour of Casco Bay to Admiral Peary’s Eagle Island on an old lobster boat with Atlantic Seal. Looking for something quieter? How about a two hour cruise (or a sunset cruise) on an antique wooden schooner built in Maine? Portland Schooner Co. has two of them and offers several daily cruises.

Were you thinking of whale watching and/or puffin watching, or even seeing lighthouses from the water side? There are whale watching cruises and lighthouse cruises from Boothbay Harbor, just a short drive from Freeport. If you want a puffin cruise, you can find one in New Harbor, just a bit farther north.

If lighthouses are something you want to see, we have lots – over 60 of them! Some, of course, you can only see by boat. Others may be too far away (Maine has a LOT of coastline, you know!). However, there are at least eight within an hour’s drive from Freeport (that doesn’t count the ones you can see on distant islands off the coast), and another 4 or 5 if you extend the distance to an hour and a half drive. Since lighthouses can be in remote areas, we also supply our guests with maps and directions or GPS coordinates of the places where they can be found.

If you’re looking for a bird sanctuary or a working historic farm, you’ll find those right here in Freeport. Mast Landing Bird Sanctuary is a serene Maine Audubon Society property, with trails to walk, places to picnic and, of course, bird watching. Not far away is Wolfe’s Neck Farm, where cows, pigs, sheep and chickens may be seen at this organic farm on the shores of Casco Bay.

If you can only stay for a day, you’ll have some tough choices to make. You may want to consider more than one day…

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