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Cozy winter getaways

October 31, 2019

As the autumn leaves descend and the temperatures drop, we’re reminded of the busy holiday season and long winter months ahead. While we may miss the warmth and freedom of summer, there is something magical about the winter season as the world gets quiet and snow canopies form between the trees. Whether you’re looking to brave the cold and explore the beauty of the outdoors, or prefer staying cozy by a crackling fire, there are many ways to embrace the winter months. Here are a few of our favorite winter weekend escapes to warm your spirits this season.

Old New England style houses in Camden, Maine with trees surrounding it.

Camden, Maine

Camden is stunning in the winter and a top pick for a few days away. With some wonderfully curated boutiques open year-round, a few great restaurants to cozy up in, and phenomenal hotels, it makes our list every time.

Since 2013, Camden has hosted a week-long celebration of winter, appropriately called Winterfest. Starting February 2nd with ice carving, winter activity demonstrations and a polar plunge in the iconic harbor, Camden melts away the winter chill. If you have little ones in tow, be sure to visit the family movie night at the Library and the Toboggan National Championships. And at the end of the day, warm up with craft cocktails and small plates by the fire at the Vintage Room, an opulent and intimate bar in the 16 Bay View hotel.

The side of a rocky cliff with a sprinkling of snow, with tall pine trees surrounding it.
An old New England hotel living room with check carpet and a dark wood fire place.

Portsmouth, New Hampshire

Portsmouth is a beacon welcoming weary travelers to marvelous New Hampshire hospitality. With such a vibrant community of local boutiques and vendors, Portsmouth makes the perfect destination to cross people off your holiday shopping list and embrace the beauty of the season. The Hotel Portsmouth is ready to greet you and those you’ve brought. Leave your baggage at the door and stroll into the beautifully curated boutique hotel with roots dating back to the 1800’s. The leather Chesterfield sofa in the parlor will be a comfortable place to unwind with friends and family.

The historic port town of Portsmouth, New Hampshire with Christmas lights.

As you meander through the historic port town you will find something for everyone you know. The best part of Portsmouth is that there are so many warm and renowned places to stop and grab a bite or drink. Portsmouth Brewery is the best stop for sustainably focused and locally crafted beers, and if you are feeling a handcrafted cocktail they have a full list. Before your weekend is over, visit Prescott Park for some Instagram worthy shots of the breathtaking scenery on your way to the Strawbery Banke Museum. Brush up on your history, or head straight to the ice rink at Puddle Dock Pond and skate your way to the end of a memorable stay in Portsmouth.

Newburyport, Massachusetts

Streets lined with wreaths, storefronts adorned with twinkling lights, restaurants humming with season’s greetings, Newburyport will keep you cozy as we head into the colder months. This town is the place to take a long weekend, unwind, and snuggle up by the fireplace. The best time to go is during a week with Invitation night. Happening every Friday in December leading up to the week of Christmas, the buzz is palpable. Every shop and restaurant has put their best foot forward, creating the warmest shopping and dining experiences around. Casually stroll from shop to shop downtown where you will find live musicians, cocktails on offer, and a vibrant display of cheer. If you need a break from the bustle of downtown merriment, the snow dusted beach of Plum Island offers a tranquil retreat just minutes away.

A view of Plum Island in the snow.
A large, red painted wooden cabin on a snowy hillside, surrounded by forest.

The Berkshires, Massachusetts

Norman Rockwell perfectly captured the spirit and magic of New England during winter. He put Stockbridge on the map, and people have loved visiting the town that inspired his painting since. Stockbridge, and the Berkshires in general, is the quintessential small New England town that many think of when they think “old world America.”

A girl lying in the snow making snow angels.

Head out Friday and plan to be gone until Monday because there is plenty to take advantage of, including some delightful time alone. The historic Getaways Inn in nearby Lenox is the perfect place to stay cozy with an aperitif, read a book, and watch the snow fall through frosted windows. Get the most out of the weekend and adventure to Hilltop Orchards. Offering cross country skiing and snowshoeing, take a stroll through the beautifully groomed trails and rediscover the nature around you. This is our favorite place to take pause to enjoy the serenity and peace of a quieter time of year. Once you’ve conquered the trails, or fallen too many times in the snow, the iconic red barn you departed from is ready to warm you up with wine, small bites, and a warm fire.

As we trade leaf peeping for snow flake catching, don’t forget to take time for you and enjoy the changing seasons. Just make sure to pack your warmest hat, coziest scarf and embrace the magic of the season.

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