Small Town Charm - Freeport, Maine

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Freeport, Maine is a hot Summer destination where tourists flock to, but during the Winter it turns into a small town filled with everything a snow bunny would dream about. Not only is the city a beautiful getaway, the vibe is filled with that of a small port town on the coast a few hours North of Boston, Massachusettes. You may remember from my previous post this week about on everything Christmas oriented that tickets through Boston are at an all time low during the month of January. The past Winter seasons I’ve taken full advantage of this and planned trips to Boston, Rhode Island, Vermont, New Hampshire and Maine.

Upon arriving into Freeport we quickly checked into the Candlebay Inn which is a quaint Bed and Breakfast (and dog friendly!) blocks near the downtown square. The rooms are filled with lovely quilt bedding, rustic shipyard flooring and floral wall paper. The house dates back to the 1800’s and has so much charm I squealed with delight upon arrival. After settling in and a quick change of clothes we headed to the downtown square to enjoy seafood at Linda Bean’s Kitchen. After dinner a stroll around the quiet town was a perfect choice for the evening. It gets dark around 4:00pm so after a few drinks we headed back for a good night’s rest.

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After awaking the next morning to a made to order breakfast from the owner’s I bundled up in layers of flannel plaid, overalls, fur lined snow boots and a cozy navy peacoat. Not wanting to waste any time the next morning, we headed out to explore some of the cities sweetest spots and stumbled across LL Bean’s flagship store. Because the area is a popular Summer destination and tourist spot during the warmer months we were surprised to find there is tons to do during the daytime and no shortage of stores. I picked up a new pair of boots at Bass Co (showcased towards the end of this post) and a few other items.

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The night before I chose a cozy ruffled sweater, sweater skirt (quickly switched out with a longer velvet midi skirt), boots, and a long wool cream colored jacket. The best way to fight the cold if you are a Southerner is to wear layers! Lots of layers! Don’t be a afraid to add scarves, hats, gloves and tights for added warmth. You can look chic without frumpy if you plan in monochromatic schemes and longer coats.

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Freeport is also a small port city for fishing and stopping by the Fisherman’s Wharf is a fun place to sight see. You have to drive through a few picturesque neighborhoods to locate the port, but as soon as you arrive you will quickly find a winter wonderland to explore.

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Frosty’s is also a fun experience and local donut shop! It was closed during the day we were there, but I intend on visiting next time I come! I recommend when visiting the Village Station where all of the retail stores reside. This was one trip where I brought an extra bag anticipating added winter items to my wardrobe for the following years travels. Down South, our clothes are made with lighter weight fabrics and you just can’t beat the steals and discounts after Christmas by stopping by the stores in the North.

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My flannel shirt was getting a little warm and decided it would be good to switch out for a thermal top and lower top wool boots with charming red laces from G.H. Bass Co. They are such a great find and highly recommend them for snow or hiking. They are made to be an outdoor shoe and found as long as the snow wasn’t higher than 8 inches, they kept my feet dry.

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Breweries and Distilleries are all over the place. Before hitting the road for more site seeing we visited the Maine Beer Company where you can have beer flights based on your palette. You literally pick four different beers after sampling and enjoy around small tables. The presentation came in small beer glasses on a chalkboard serving tray to remember which beers you picked during your order.

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The last stop made was to the Cold River Distillery was the last stop before heading on to the next city for the New England road trip. They only serve a very small selection of gin and vodka but craft delicious cocktails and the liquor was so smooth it can be enjoyed by simply taking a sip or two with nothing added. They have a very unique process for how they make their liquor and as much as I wanted to bring a bottle back, it’s very difficult due to state regulation laws. I highly recommend trying their tastings if you have a few minutes before heading out.

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Where are you dreaming of heading to the start of the year? Any fun ideas in mind for winter destinations?