Weekend in Freeport, Maine

One of my favorite things about living in Boston is that it’s easy to go away for a weekend getaway. Whether it’s a preppy jaunt to Kennebunkport or a girls’ day trip to Newport, everything in New England is a short drive away.

On our last New England getaway, my boyfriend and I visited Freeport, Maine for 3 nights over the extended New Years Eve weekend. Neither of us had ever been to Freeport and to be honest, it wasn’t on our top list of places to visit in New England. But as luck would have it during my lodging search, I found an adorable place on Airbnb that was perfect for a romantic weekend away.
airbnb freeport maine

If you haven’t used Airbnb, you must check it out (here’s a link for $20 off your first trip). For those unacquainted, Airbnb is a website that facilitates lodging between homeowners with extra rooms or guest houses and travelers seeking the comforts of home-like accommodations. I love, love, LOVE Airbnb and no one paid me to say that!

We stayed in a converted barn just south of downtown Freeport. Since Freeport is close to Portland, we had originally intended on staying in the area and spending at least at day in Portland. But between the food, shopping, and outdoor activities in Freeport and the cozy fireplace and outdoor firepit at our Airbnb, we spent the entire weekend in town.

minglewood airbnb freeport maine

couple drinking coffee by the fire

airbnb freeport firepit

Dinner at Gather Maine

Just two hours north of Boston, my boyfriend and I drove up to Freeport the evening of New Years Eve with enough time to check into the Airbnb and change before our dinner reservations. Thanks to recommendations from coworkers and some Yelp reviews, we reserved a table at Gather in Yarmouth. The farm to table restaurant was perfect for a relaxing New Year’s Eve dinner, complete with a special menu, delicious cocktails, and a bluegrass jazz band. The rabbit I ordered from the special holiday menu was outstanding and my boyfriend’s salmon with fried kale was amazing!

dinner at gather maine

Gather wasn’t having a big New Year’s celebration, which worked with our low-key celebration plans of drinking bubbles in our pajamas so after dinner we drove back to our cozy weekend home to ring in 2016.

Freeport Village

Though small, the downtown area of Freeport, called Freeport Village, packs a strong punch. We spent hours casually strolling through the LL Bean stores (there’s at least 4 of them) and the various outlets.

ll bean freeport maine

We fell for the tourist trap and ate lunch at Linda Bean’s Topside Tavern, a restaurant directly across from the LL Bean flagship store. If you’re looking for food in the area, I recommend walking a block or two north on Route 1 and checking out some of the other restaurants or driving a few minutes down the road for brunch at the Muddy Rudder, lunch and beer at Gritty’s, or a hearty dinner at Buck’s Naked BBQ . Or if you’re craving something sweet, stay in town and head to Frosty’s Donuts for a glazed bite of heaven.

gritty mcduffs restaurant freeport maine

frostys donuts freeport maine

Wolfe’s Neck Woods State Park

Despite a warm fall and beginning of winter, a few inches of snow fell in Freeport before we arrived. We took this opportunity to break in the new snowshoes my boyfriend bought us for the holidays at Wolfe’s Neck Woods State Park. Our thoughtful Airbnb host had put together a binder of information, including a trail map of the coastline park so we were well prepared for a snowy walk through the woods.

snowshoe wolfes neck state park freeport maine

wolfes neck state park

snow shoe wolfes neck state park

Maine Beer Company

Since no weekend trip is complete without a trip to a local brewery, Maine Beer Company was the last stop on our Freeport weekend getaway. My boyfriend and I split a flight of four beers (Mo, Beer III, Another One, and Pilot 9). Breweries can be hit or miss when it comes to food, as the licensing limits what they can and can’t serve, but the pretzels at Maine Beer Company were on point. Fresh and delicious and served with a side of tasty mustard, the pretzel was the perfect compliment to the beer flight.

maine beer company freeport

maine beer company freeport

If you’re looking for a relaxing weekend getaway close to Boston, I highly recommend checking out Freeport!

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