12 Best Destinations for a Winter Vacation in Massachusetts
Massachusetts is a quintessential New England gem state, defined by its breathtaking coastlines and beaches, historic attractions, and quaint small towns. Naturally, people flock to the Bay State in summer to enjoy its gorgeous beaches and coastal scenery. However, winter comes with a special allure, and for those who can stand up to the cold, it is one of the best seasons to visit this historic state. While the beaches and coastline will be scanty, there will be numerous frozen lakes, waterfalls, and snow-filled landscapes for holiday photo ops, as well as plenty of winter sports to enjoy. From the Jiminy Ski Resort to the frozen pond in Boston Common, find the top 12 destinations to enjoy a winter vacation in Massachusetts.
Blue Hills Ski Area, Canton
The Blue Hills Ski Area is a winter getaway to ride out the season and make the most of the snow. Although smaller than most ski resorts, the skiing and snowboarding experiences are no less thrilling here. Also, it offers an escape from Boston to appreciate a true outdoor winter experience since it's the closest ski resort to the city.
The resort has 60 acres of skiable terrain, a vertical drop of 309 feet, 12 trails, a terrain park, and four lifts. The ski trails have 90% snow-making capabilities, and there are different runs for beginners, intermediate, and advanced skiers to explore. Night skiing is also available, and lodging is possible at the Hilton Garden Inn Boston Canton, which is less than five minutes from the slopes.
Rockport
Rockport is a magnificent coastal town on Cape Ann, perfect for a winter vacation, as snow and its whitish aura saturate the area’s coastal scenery. The season is also a lovely time to explore the town's beaches, such as Front, Old Garden, and Long Beaches, as they will be less crowded and assume new picturesque looks that deserve a camera.
Winter vacationers can also leverage the season to dive into the town’s art scene as over 20 art galleries are available to visit, notably the Art Nook, Scott Tubby Fine Art, the Art of David Arsenault, and IArtColony. Events like the Annual Rockport Christmas Pageant, Christmas in Rockport, and Winter Warmer on the Greenway make the season more fascinating. Meanwhile, Emerson Inn and Rockport Inn and Suites are the top accommodations in town for staying the entire season.
Boston Common Frog Pond, Boston
The Boston Common Frog Pond is a favorite destination for locals and visitors to Boston in winter, as it offers one of the city's most exciting and thrilling winter sports, ice skating. This sport has been a favorite in Boston for many years since the Boston Common is the oldest public park in the country. Very few experiences can match up to ice skating on the Frog Pond, which is usually open from November to March. Family, friends, lovers, and just anyone who loves to ice skate are invited to this spot in winter to have fun and create memories.
During the Christmas season, the experience hits a new high as the Christmas trees and twinkling lights surround the pond. These lights are even more magical and picturesque at night, making it the perfect for a romantic date. For those looking to spend the night in the city, accommodations close to this pond include The Godfrey Hotel Boston and Newbury Boston.
Canterbury Farm, Becket
The Canterbury Farm is a regular farm in the summer with hiking trails and guided hikes, but it is a winter wonderland once the temperature drops. This farm offers cross-country skiing, snowshoeing, ski rentals and lessons, and ice skating on its pond. It boasts over 19 miles of well-groomed ski trails for beginners, intermediate, and advanced skiers, while its snowshoe trails weave through the nearby lush forests. Visitors can snowshoe across the specially designed snowshoe trails to see lakes, brooks, beaver ponds, snowcapped mountains, and fields, relishing each view while looking forward to the next. The farm also has a lodge for visitors who would love to stay longer.
Nantucket
Nantucket is a small, secluded island town and summer tourist destination 30 miles from Cape Cod that charms everyone with its captivating oceanside scenery. In winter, the views become like a scene out of a fairytale movie, as snow descends on the landscapes. Even better, there are fewer crowds in winter so visitors will have the island’s views and attractions to themselves. Once here, visit beaches like Sconset and Madaket to capture the picture-perfect sunsets and late sunrises while admiring wildlife along the coast, such as seals that appear in the cold season.
Next, head to Brant Point and Sankaty Head Lighthouse to take holiday photos with the idyllic backdrops. Also, the Nantucket Whaling Museum is an ideal spot to enjoy indoor warmth while exploring. The museum houses various artifacts of whaling vessels and the skeleton of a massive sperm whale. For extended stays, the Nantucket Inn is a premier accommodation to check out.
Butternut Ski Resort, Great Barrington
The Butternut Ski Resort and Tubing Area in Great Barrington overlays on Warner Mountain in the Berkshire Region and offers mind-blowing winter experiences. This winter wonderland features 100 acres of skiable terrain and 22 trails designated for beginners, intermediate, and advanced skiers. It also features a vertical drop of 1,000 feet, two terrain parks, ten lifts with four quad lifts, a reserved area for tubing, and all trails are outfitted with snow-making capabilities.
The resort is a winter getaway, perfect for family or solo travelers who want to embark on skiing, snow tubing, snowboarding, and snowshoeing adventures, among other winter activities. Meanwhile, there are lodgings nearby for longer stays, like the East Rock Inn in Great Barrington and Red Lion Inn in Stockbridge.
Trap Falls, Ashby
One of nature's natural wonders comes in a frozen waterfall, and Trap Falls in Willard Brook State Forest, Ashby, is a typical example. For winter vacationers seeking scenic escapes and magical views, the falls offer this unique experience and serve as a scintillating backdrop for holiday photoshoots. This attraction is easily accessible with a 0.1-mile hike from the Willard Brook State Forest and is mostly secluded since winter is an off-season. Admire these frozen natural beauties that come in three cascades with the highest drop at 12 feet, and remember to take in the views with a camera.
For lodging, the Great Wolf Lodge in nearby Fitchburg boasts four-star accommodations for guests and a basecamp to explore this winter spectacle.
Concord
Concord is a beautiful small town in Middlesex County, offering some of the best winter experiences in Massachusetts. There are several events and activities to undertake while here, making the season festive and memorable. First off, the town’s Winter Wonderland in January is a free, delightful event for families and friends, featuring horse-drawn sleigh rides, sledding, good eats, and music. Also, winter in this town is a great time to explore the paths of history at the Concord Museum, where artifacts and exhibits mirror the area's ancient days.
In addition, Valley Sports Area has an ice skating rink for winter sports lovers to revel in. However, Walden Pond is a more enthralling destination that screams of winter and snow. The pond has no off-season, but winter makes it a hub for ice skating, ice fishing, hiking in the snow, and cross-country skiing. For lodging throughout the season, the Concord Colonial Inn is one of the best accommodation options in town.
Bash Bish Falls, Mount Washington
Take an unforgettable winter hike to the magical Bash Bish Falls in the town of Mount Washington, which freezes over in winter. This fall is the tallest in Massachusetts, which makes it more inviting and the views more wondrous. Find the falls at the border with New York, where it draws crowds from Massachusetts and New York during the peak seasons, making winter the perfect time to visit for those avoiding the crowd. Beyond the frozen cascading marvel, the rock formations around are also visually enticing as they are capped and saturated with snow.
While the hike is short, at 0.6 miles, the views of rock formations clothed in white and a frozen, 80-foot-tall fall are rewarding and captivating. Don’t forget to spend the night at nearby accommodations like Fairfield Inn & Suites By Marriott Great Barrington Lenox for a more satisfying experience.
Wachusett Mountain, Princeton
The Wachusett Mountain in Princeton beckons skiing enthusiasts, snowmobiling fans, and every other winter sport-loving tourist to visit its terrain for memorable experiences. The resort prides itself on its reputation as the most accessible ski area in Massachusetts, with more than 20 trails, more than five lifts, and a 1,000-foot vertical drop. There are various trails for beginners, intermediate, and advanced skiers so everyone can have fun across its 110 acres of skiable terrain.
Visitors can enjoy adrenaline-pumping skiing, snowboarding, cross-country skiing, and snowshoeing activities. Furthermore, the resort’s trails are equipped with snow-making capabilities, and night skiing is available in some areas. Thankfully, there are lodging services for extended stays, such as the nearby DoubleTree by Hilton Hotel Leominster.
Stockbridge
The town of Stockbridge is a premier winter destination for sensational experiences. Once here, even taking a stroll on its historic main street dotted with snow-drenched 18th and 19th-century structures is a delight in itself. However, the town presents more amazing ways to enjoy the season. History lovers can start by visiting the Norman Rockwell Museum to see over 500 authentic paintings of Norman Rockwell and more than 100,000 other items, including photographs.
For ice-fishing aficionados, the nearby Stockbridge Bowl is a 372-acre pond in town offering exciting ice-fishing expeditions in winter. Also, winter is a great time to visit the Stockbridge Library to see over 500 artifacts and stroll through the beautifully lit trees. Meanwhile, The Inn at Stockbridge or Red Lion Inn are ideal lodging destinations to enjoy the entire winter season in town.
Jiminy Peak Mountain Resort, Hancock
Located in the Taconic Mountains in the town of Hancock, Jiminy Peak Mountain Resort is famous as the largest ski resort in Southern New England and one of the best places for a winter vacation in Massachusetts. The resort is a winter wonderland with varied winter sports and activities and offers lodging on-site.
Winter sports lovers can enjoy 170 acres of skiable area, 45 trails, three terrain parks, and nine lifts with two magic carpets. Prime winter sports activities in the park include skiing, snowmobiling, and night skiing for those who want to enjoy the views and feel the thrill of adventures.
Winter is an incredibly special season in the US, with a sensational snowy aura complemented by the vibes of the festive season. In Massachusetts, it is as spectacular as they come, with the state receiving about 42 inches of snow annually. Once the season is in full swing, the Bay Stay comes alive across several destinations where nature, fun, thrill, and memories abound. From ski resorts and frozen water bodies to indoor attractions like museums and galleries, these destinations are truly magical in winter and worth visiting for incredible experiences.
