November 29th, 2023

Enjoy the Snow with the Best Skiing near Great Barrington

As the first blanket of powder covers the ground, snowfiends from all over flock to embrace the exhilarating thrill of skiing in the Berkshires. Nestled in western Massachusetts, this picturesque region transforms into a winter wonderland, offering a collection of snowy peaks and groomed trails that welcome experts and novices alike. This chilly season, test your downhill skills and take to the slopes! Not sure where to start? Here are our favorite skiing areas near Great Barrington, MA.

Stay at Briarcliff Motel

Jiminy Peak

Jiminy Peak Ski Resort
Source: Jiminy Peak

About 40 minutes away from the Briarcliff Motel, you’ll find Jiminy Peak, the biggest ski resort in southern New England. Known for its family-friendly atmosphere, night skiing, and snowmaking capabilities, this ski area has over 45 skiing and snowboarding trails covering over 167 acres. They also offer lessons for skiers and snowboarders of all ages and abilities, a village of restaurants and shops at the base of the mountain, and special events throughout the year. 

Catamount Mountain Resort

Catamount Mountain Resort is one of the biggest resorts in the state and only a 20-minute drive from the Briarcliff Motel. Offering some of the most varied terrain in southern New England, this ski area is suited for skiers and snowboarders who flex all skill sets. For those who prefer to take the day a bit slower, they also have a variety of cozy restaurants and bars, perfect for an aprés ski cocktail or a cup of steaming hot chocolate. 

Otis Ridge Ski Area

Looking to up your skill set on the slopes? At Otis Ridge, the majority of trails are blues and greens—there are only two black diamonds—making it the perfect place for beginners to challenge themselves and gain more confidence on their skis or board. A smaller mountain with an emphasis on community, this ski area has been spreading a genuine love for snow sports since it opened in 1946. They also offer kids programs and lessons for those who seek a bit more guided direction when it comes to technique and strategy.

Ski Butternut

If you drive less than 10 minutes down the road from the Briarcliff Motel, you’ll find yourself at Ski Butternut. This quaint and welcoming ski resort lives by the underlying philosophy of maintaining a proper balance between growth and intimacy. Here, they believe that skiers should be offered a lovely, uncompromised winter environment to ski through—and this is why they focus their efforts on making ski days at Butternut truly memorable experiences. If you’re a skier who seeks the untouched natural beauty of the mountain, Ski Butternut is for you. 

Bousquet Mountain

Established in 1932, Bousquet Mountain is the Berkshires’s oldest existing ski area—and it’s just as loved now as it was then. Only 20 minutes away from the Briarcliff Motel, this ski area welcomes locals and visitors who love winter, snow sports, and Bousquet Mountain. They’re big into timeless traditions while also embracing new experiences that grow the community. With a variety of trails, you’ll be in love with Bousquet Mountain by the end of the day, too.

Stay at Briarcliff Motel 

What’s the thing you’ll crave most after a long day on the slopes (well, after an aprés ski beverage, of course)? A warm, fluffy bed with plush pillows and a dreamy duvet. This is what you’ll find at the convenient and charming Briarcliff Motel. So go ahead, grab your lift ticket, and book your room—the mountain is calling.