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Pittsfield Today
By the People, for the People
The Berkshires Offers Romantic Getaways for Valentine's Day
From sleigh rides to cozy dinners, the Berkshires region has plenty of options for couples this Valentine's Day.
Published on Feb. 13, 2026
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The Berkshires region of Massachusetts is a popular destination for romantic Valentine's Day getaways. Couples can enjoy activities like horse-drawn sleigh rides at Sweet Brook Farm, wine tastings at local wineries like Furnace Brook Winery and Balderdash Cellars, and intimate dinners at charming bistros such as Café Triskelle.
Why it matters
The Berkshires is known for its natural beauty, quaint towns, and abundance of activities that cater to couples looking for a romantic weekend escape. With Valentine's Day approaching, the region provides the perfect setting for those seeking a cozy, intimate setting to celebrate their relationship.
The details
The Berkshires offers a variety of romantic experiences for Valentine's Day. Couples can bundle up and take a horse-drawn sleigh ride through the picturesque winter landscape at Sweet Brook Farm in Williamstown. For those looking to enjoy some local libations, the region is home to several popular wineries, including Furnace Brook Winery in Richmond and Balderdash Cellars in Pittsfield. When it comes to dining, Café Triskelle in Lee, formerly known as Chez Nous, is a top-rated French bistro known for its charming, cozy atmosphere.
- Valentine's Day is celebrated annually on February 14.
The players
Sweet Brook Farm
A farm in Williamstown, Massachusetts that offers horse-drawn sleigh rides.
Furnace Brook Winery
A winery located in Richmond, Massachusetts.
Balderdash Cellars
A winery located in Pittsfield, Massachusetts.
Café Triskelle
A French bistro located in Lee, Massachusetts, formerly known as Chez Nous.
The takeaway
The Berkshires region offers a variety of romantic experiences for couples celebrating Valentine's Day, from cozy sleigh rides and wine tastings to intimate dinners at charming local eateries, making it an ideal destination for a weekend getaway.
