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An Adventurous Day in Freeport: 12 Fun Things to See and Do at Christmastime

FREEPORT, Maine – Freeport is a fun place to visit any time of year, but most especially now during the big holiday season. From the Sparkle Celebration to the Northern Lights Celebration, the festive wreaths and decorations and displays, the horse-drawn carriage rides, the food, the beer, the entertainment and so much more—all combine to make a visit to town at Christmastime so much more than just a shopping excursion. Park your car, walk around, explore and see for yourself.

To whet your holiday whistle for a Freeport adventure, here are a dozen different things to see and do over the course of a daylong visit, so lace up your walking shoes, put on a warm hat and coat, and make the trip. And don’t forget to bring your shopping list… it is Freeport after all!

Try these dozen things to see or do for a full-on Freeport holiday adventure. Photo © Carey Kish.


Start your adventure with a cup of coffee and a yummy donut at Frosty’s, tucked in just off Main Street behind the Freeport Historical Society. The venerable donut shop, an institution in nearby Brunswick for, well, almost ever, opened the Freeport store a couple years ago. Can’t choose between the many different varieties? Understood. Get a half-dozen then, or maybe a dozen and take some home.

Get your fill of donuts and coffee at Frosty's. Photo © Carey Kish.


Housed in the Harrington House—a beautiful brick and granite Greek Revival-style building built in 1830 by Freeport merchant Enoch Harrington—is an amazing array of artifacts and archival materials that capture the rich history, culture and fabric of Freeport. From artwork, furniture, textiles and household items, musical instruments, toys, tools and archaeological objects to manuscripts, maps, newspapers, photos, postcards, diaries and much more, the Freeport Historical Society‘s collections are a treasure trove of town history.

The Freeport Historical Society captures the rich history, culture and fabric of Freeport. Photo © Carey Kish.


Freeport is a shopper’s paradise for sure, where pretty much everything under a winter’s sky can be found amid the eclectic mix of national retail outlets with the familiar names to the many locally-owned stores. It’s easy to cruise along Main Street and just browse the shops there, but have you really explored the many great shops down the side streets? Meander a bit and discover; you may be surprised at what you find!

More than 200 shops, inns, restaurants and attractions are found in Freeport. Photo © Carey Kish.


When a bite of lunch becomes the order of the day, duck into the Topside Tavern at the corner of Bow Street and Main Street for a lobster roll and a cup of chowder. The quarter-pound lobster roll is good, but The Colossal is even better. Chips, pickle and cole slaw make it quite a hearty meal, perfect to keep you going through the afternoon.

The extensive “Maine experience” menu is chock full of other fresh dishes, so take your pick. Owing to Linda Bean’s “trap to table” business vision, the restaurant sources only Maine lobster and as many other locally produced foods as possible, with an eye not only toward fresh food but good jobs too. Sustainability baby!

Linda Bean's Perfect Maine Lobster Roll: The Colossal. Yum! The Colossal


Who doesn’t love a good book store? Indeed. And Sherman’s is at the top of my list and has been for a long, long time, ever since my teenage days of exploration far and wide when I would wander off to Bar Harbor and browse the shelves at the original Sherman’s there.

Speaking of, did you know that Sherman’s is the oldest book store in Maine, the Bar Harbor shop having opened its doors in 1886. Wow. I don’t know how long the store on Main Street in Freeport has been there, but I’d venture a while. It’s always fun to poke around for an interesting title, and maybe come away with a fun gift or two (they sell gifts, stationary and toys and whatnot too).

It's books galore and more at Sherman's. Photo © Carey Kish.


By now you must no doubt be getting thirsty; I know I am! Time to head a short ways out of downtown to get a beer then, because after all, “what is better than beer?” This great quote is from the most excellent story of the brothers who founded the Maine Beer Company out of a simple passion for beer. Oh my, can we ever understand that feeling!

The tasting room features 8 mighty fine beers on tap, including some brewery-only releases, plus local snacks, bottled beer to go, and some cool beer-related gift stuff. Order up a small or large “dinner,” a flight, or go big for “the all in.” Then hang out and enjoy and watch the brewery ops below through the big glass windows.

Get your fill of good Maine beer at the tasting room of the Maine Beer Company. Photo © Carey Kish.


OK, so you’ve had donuts, a big lobster roll and a beer or two. Best if you walk some of it off, wouldn’t you say? A good way to do just that is by following along on the Freeport Heritage Trail, a self-guided walking tour of the historic Freeport village. The trail meanders through town visiting ten spots en route, from the Old First Parish Burial Ground and Meetinghouse to L.L. Bean and Jameson Tavern to Derosier’s Market and the Frost Gully Pumping Station.

Interpretive signs complete with historic photos and descriptive text tell the many stories as you go, from shipbuilding, trading and shoemaking to tourism and retail . More stops on the “trail” are found out in the Wolf’s Neck area.

Walk through history on the Freeport Heritage Trail. Photo © Carey Kish.


This family-owned and operated inn has been offering classic Maine hospitality since 1984. The antique-filled hotel features two award-winning restaurants, the Maine Harvest Dining Room and the Broad Arrow Tavern, as well as more than 90 comfortable rooms, fireplaces, Jacuzzis, an indoor pool and more.

You don’t have to stay at the Harraseeket Inn (but you could!) to experience its warmth and charm, however, because every day between 3:30 and 4:30, traditional afternoon tea is served in the Drawing Room, where visitors and guests alike are invited to enjoy a relaxing cup of something hot, tea of course, but also cocoa, hot mulled cider or eggnog (varies daily), as well as wonderfully prepared finger sandwiches, foodie bites, fresh fruit and sweet treats. Tea is quite the affair; do stop in!

The family-owned Harraseeket Inn has been catering to Freeport visitors since 1984. Photo © Carey Kish.

Afternoon tea in the Drawing Room at the Harraseeket Inn is a wonderful affair. Photo © Carey Kish.


Saunter over to the big Christmas tree in Discovery Park next to the L.L. Bean flagship retail store for an extravaganza of beautiful holiday music and visual effects. The tree is decorated with 25,000 lights that are synchronized to a variety of delightful holiday tunes. The amazing display goes on every half-hour daily from 5 to 9 p.m. though New Year’s Eve. Nothing like a wild Christmas light show set to Manheim Steamroller to get you in the holiday spirit! When the show concludes, step inside the big store and mill around, because everybody needs something from L.L. Bean, especially this time of year!

The Musical Holiday Light Show at L.L. Bean is a terrific experience. Photo © Carey Kish.

Everybody needs something from at L.L. Bean at Christmastime! Photo © Carey Kish.


The Azure Café keeps me coming back again and again, and for good reasons: the food is outstanding always, the wine selection is terrific, the service is beyond wonderful, and the atmosphere is quiet and comfortable. From a wide range of Italian specialties to many and varied fresh seafood dishes, this place shines oh so bright. Dinner here is an experience for sure, a relaxing several hours where everything outside the window is, well, out there, allowing your focus to truly be on the good food and the good company.

The Azure Café serves up the very best calamari on the planet, a fine starter to any meal. Rice vinegar is the key I’m told. Love it. For dinner on our recent visit, my wife enjoyed the ravioli zucca, a fine dish of ricotta cheese and sage roasted butternut squash and spinach chiffonade in a pine nut parmesan cream sauce, while I feasted on the veal saltimbocca lightly sautéed with prosciutto, sage and mozzarella in white wine and lemon herb butter, served over linguine. Oh my. Sadly, dessert this time around was not even an option.

Enjoy a most wonderful dining experience at the Azure Cafe. Photo © Carey Kish.

Mai I recommend the calamari as an appetizer?! Photo © Carey Kish.

And the veal saltimbocca as an entree? Oh my! Photo © Carey Kish.


This state-of-the-art cinema located in Freeport Village Station always has a great selection of the latest Hollywood films playing on its six big screens. High-back rocking chair seats in each of the stadium-style theaters make for an extra comfy movie-going experience. Grab a big bag of popcorn and settle in for a good flick. Enjoy!

Enjoy a movie and popcorn in style at the Nordica Theatre. Photo © Carey Kish.


On US Route 1 in South Freeport is one of only two big Native American statues in Maine. Locals know it as the BFI or FBI. Go see it, get a photo, say you’ve been there. It’s part of the adventure after all…

For more info on all there is to see and do in Freeport: Visit Freeport USA or call 207-865-1212.

The BFI. Photo © Carey Kish.


The big freshwater fish tank at L.L. Bean is a pretty cool thing to see no matter what your age. Photo © Carey Kish.

The Harraseeket Inn is a pretty fine place to spend an evening, an more affordable than you might expect. Photo © Carey Kish.

The blueberry pie at Linda Bean's Maine Kitchen and Topside Tavern was might good. Photo © Carey Kish.