Our Area Guide book

Welcome to Freeport

Freeport is the ideal destination for exploring the Maine Coastline! In addition to Freeport being loaded with shopping (Yankee Magazine voted Freeport as a favorite shopping destination), it also has beautiful State Parks, stunning coastal areas, hiking trails, gardens, museums, farms, history, and nature.  

A short list of just some of the things to do & see in Freeport

Scroll down for some rainy day recommendations! 

  • Freeport LOVES it's festivals and events. Weekly free summer outdoor concerts, town-wide art fairs, Fall festivals, and it's famous Holiday Sparkle Celebration. 
  • Take Seascoast Tours out to Eagle Island! Seacoast Tours does a great boat tour of the islands off the Freeport coastline, but it also includes a two hour stop-over on Eagle Island! Read all about the tour here. We love it for it's beauty, but it's also a great place to take a picnic lunch, or your sketch book! 
  • LL Bean's Flagship Store and LL Bean Outdoor Adventures Take a look at their website and sign up for an outdoor class! Click here to see their schedule of events on the town green - including free yoga during the summer
  • Cafes and Restaurants we love in Freeport: Petrillos, Jameson Tavern, Harraseeket Lunch & Lobster in South Freeport, Brickyard Pizza, Maine Beer Co, and the Sunrise Cafe for a great breakfast!
  • Art Galleries in Freeport are all wonderful (we reallyLOVE Abacus!), Sherman's Bookshop, The British Goods Store, Leapin' Lizards, and Mexicali Blues are our go-to spots when we feel like shopping. 
  • Freeport Performing Arts Center & Freeport Community Players
  • Freeport's Famous Outlets, including everything from clothes to pottery outlets! 
  • Pettengill Farm. Our favorite walk in Freeport! A beautiful place that takes you back in time. Click here for more information!  
  • Wolfes Neck State Park
  • Wolfes Neck Farm, Camping, and Trails
  • Winslow Park. We LOVE Winslow! Wonderful trails along the waterfront, and beautiful views all the way around the peninsula! It's a weekly stop for us year round! Turn left out of our driveway, and about 6 minutes down the road, turn left onto Staples Point Road. Winslow is at the end. 
A few favorites within 30 minutes of Freeport

  • Portland Maine, and all of it's galleries, restaurants, shopping, island cruises, and lighthouses! 
  • Pineland Farms, with over 5000 acres of open public land for hiking, skiing, biking, and more.
  • Portland Museum of Art
  • Maine Maritime Museum
  • Walking Trails and Cliff Walks in Harpswell
  • Longfellow House in Portland Maine
  • Victoria Mansion
  • Walker Art Museum at Bowdoin College
  • Museum of African Tribal Art
  • Institute of Contemporary Art at Maine College of Art
  • Casco Bay Lines, where you can catch a 3 hour mailboat run out around the islands, a boat out to Peaks island for an afternoon of walking around the island, or any number of other day adventures on the water. 
  • Merrill Auditorium
  • Too many parks, hiking trails, and nature preserves to list! 
Within an hour of Freeport
  • Maine Botanical Gardens
  • Lighthouse, lighthouses, and more Lighthouses. 
  • Portland Head Light, Cape Elizabeth
  • Two Lights, Cape Elizabeth
  • Seguin Island Lighthouse, Georgetown
  • Bates College Museum of Art
  • Fansworth Art Museum
  • Whaleback, Kittery, Piscataqua River entrance
  • Kennebunkport & Cape Porpoise
  • Wood Island, Biddeford
  • Spring Point Ledge, South Portland
  • Portland Breakwater, South Portland
  • Halfway Rock
  • Perkins Island, Georgetown
  • Boothbay Harbor
  • ... and so much more!
Ideas for a Rainy Day in Freeport 

Tour lighthouses!  In the rain & fog, light houses truly shine (literally and figuratively!). There is nothing like a walk around a lighthouse, & a careful climb around the rocks, on a cloudy day! 

Go to a museum! The Maine Maritime Museum, Portland Art Museum, Longfellow House, & Victoria Mansion are our favorites! 

Go antique shopping. Our favorite places are the the Old Mill Antique Mall in Brunswick, and Freeport Antiques right in downtown on Route 1, across from the Town Hall.   

Shop Freeport! The town is generally quieter on a rainy day. A slow wandering around Sherman's books, and a coffee from Coffee by Design make for a perfect afternoon. 

Do a Portland Tour! All of the tours in Portland are great, and they are all equipped to deal with a rainy day! If you are a food lover, there is a wonderful Foodie Tour you can go on. Check out a bunch of great Food & History Tours of Portland here

Take a drive to Orr and Bailey Islands and watch the waves come in and the rain come down while having a hot cup of chowder at Cook’s Lobster House. Bailey Island is a favorite of ours! Tons of great walking trails (we love the Giant's Staircase!) and our favorite shop for local goodies is the Lands End Gift Shop. 

... and if all of this is not enough, please check out our "Guide-Book" on airbnb by clicking below! 
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