Fall in Litchfield Hills, CT

The Litchfield Hills of northwestern Connecticut are a marvelous place to be anytime of year, but it’s hard to beat fall when it comes to stop-you-in-your-tracks beauty. The star of the landscape show this stretch of the calendar, of course, is the vibrant and multicolored autumn foliage, but there’s also plenty to do against that magnificent backdrop. Plus, harvest season brings a rich bounty, including to our table here at Winvian Farm, the perfect place to stay in the Litchfield Hills.

To whet your appetite for a Winvian getaway during these crisp, colorful, and all-around magical months, here are our five favorite fall activities to pursue in the area, presented in no particular order.

(1) Walk the Woods

Friendly weather and that fine fall foliage make autumn a fabulous time to hit the trails in the Litchfield Hills. Along with our own paths here at Winvian, you’ve got multiple serene hikes at your disposal on the lovely grounds of the White Memorial Foundation and Conservation Center, our cherished neighbor. Besides its 40-odd miles of trails, this property hosts regular events—including, coming up on September 24th, its 40th annual Family Nature Day, with raptors, reptiles, and other live critters on display, plus guided walks, live tunes, wagon rides, and more.

(2) Gallery Hop

A bevy of local art galleries and centers make another fine option for fall day-tripping out of Winvian Farm. Consider, for example, the Washington Art Association & Gallery in Washington, Connecticut, a short (and scenic) drive from our resort. Established back in 1952, the WAA Gallery has hosted better than 600 exhibitions—the current one, Home & Garden, runs through October 9th—and also offers a variety of classes.

(3) Visit a Local Brewery or Distillery

What better way to top off an afternoon of leaf-peeping in the Litchfield Hills than by toasting the fall colors and crisp air with a suitable adult beverage? You’ve got some fine options on that front, among them Litchfield Distillery, which produces small-batch spirits such as bourbon, gin, and vodka and gives complimentary tours of its facilities, and Clocktown Brewing Co., which backs up its delish craft brews with specialty cocktails and a menu anchored by wood-fired pizza.

(4) Amble Through an Apple Orchard

Indulge in a classic fall pastime on a Winvian Farm getaway by visiting one of our area’s U-pick farms and orchards. Averill Farm is one of the most notable, having been in the same family since 1746 and maintaining a 30-acre orchard with pick-your-own apples and pears. A visit to the property this time of year can (and should) also include sampling apple cider donuts and other seasonal treats.

(5) Attend a Fall Festival

The White Memorial Foundation and Conservation Center’s Family Nature Day isn’t the only fall happening to check out on a visit to the Litchfield Hills. Others include the Garlic & Harvest Festival at Bethlehem, Connecticut’s fairgrounds, underway October 8th and 9th. Specialty food vendors here will be serving up all manner of garlicky goodness, from garlic dips to garlic oils, with prepared dishes on offer in the food court as well: garlic sausage, garlic pizzas, garlic ice cream—you name it! Rides, games, cooking demos, and live music round out the flavorful proceedings.

Then there’s the Litchfield Art Festival on September 24th, an outdoor juried fine art show at Litchfield Community Field featuring local artists as well as those from farther afield in New England and beyond.

Bonus: Fall Pleasures at Winvian Farm

Of course, you’ll also be spoiled for choices when it comes to appreciating fall in the Litchfield Hills right here on our 113 beautiful acres. A few possibilities for cozying up by a crackling fire at Winvian:

  • Refine your s’mores technique around our irresistible firepit.
  • Indulge in a fireside couples massage.
  • Dine by the fire at The Restaurant at Winvian Farm, featuring farm-to-fork cuisine enhanced by our own on-site gardens and greenhouse. (Word to the wise: Make your request well in advance for fireside dining!)
  • Sip on a delicious seasonal cocktail at our new Maggie’s Tavern in front of the grand stone fireplace.

Book your autumnal escape to the Litchfield Hills with Winvian Farm hospitality today!


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