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Photograph: Courtesy CT Tourism

“Fall” for: Litchfield Hills in Connecticut

Head to the Litchfield Hills for your next autumn weekend getaway

Time Out New York in association with CT Tourism
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A private getaway for many a New Englander, the secluded, exclusive Litchfield Hills have been home to greats like Alexander Calder, Frank McCourt, Meryl Streep and Diane von Furstenberg—just to name a few. Rent a car, and it’s easy to trade a few days in NYC for some of Connecticut’s scenic towns, most scrumptious fare (with many locally-sourced ingredients) and partake in totally Instagrammable activities. P.S. Did we mention the Litchfield Hills are home to a handful of vineyards, wineries and even a brewery?

Kindra Clineff

ADVENTURE ON FOOT:

Those bitten by the antiquing bug should look no farther than Main Street in Woodbury, known as the antique capital of Connecticut and home to many beautiful historic buildings, including private residences and churches. Woodbury is also popular in the fall for its Haunted Hayride and Haunted Barn sponsored by the Woodbury Lions Club (this year, Oct 20, 21, 27 and 28)! Those interested in shopping might also venture to Kent or Litchfield town center to check out charming local gift, apparel and home décor shops.

Robie Capps

MUSEUM/ATTRACTION-HOP:

Families shouldn’t miss out on Washington’s Institute for American Indian Studies (38 Curtis Rd, 860-868-0518, iaismuseum.org), a quiet, intimate museum experience where kids can see outdoor replicas of wigwams, a longhouse and a traditional canoe. Litchfield County is also home to amusement park Lake Compounce and its seasonal Haunted Graveyard (186 Enterprise Dr, Bristol; 860-583-3300, lakecompounce.com) and local theme park Quassy on Lake Quassapaug (2132 Middlebury Rd, Middlebury; quassy.com).

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EAT:

Those visiting the area would be remiss to skip out on a trip to cozy local joints like the tavern-style White Horse Pub (258 New Milford Turnpike, New Preston; 860-868-1496, whitehorsecountrypub.com), which offers an backyard garden, or Bohemian Pizza and Ditto’s bar, an awesomely funky haunt with a huge fireplace that (was, at least) decorated nose to tail in fun graffiti and album covers—oh, and the best thin-crust pizza in town (342 Bantam Rd, Litchfield; 860-567-3980, bohemianpizza.com). It reopens this fall. The ambiance at The G.W. Tavern also can’t be beat, with indoor-outdoor seating, live music and a menu loaded with comfort foods like crab cakes, macaroni and cheese and hearty Kobe burgers (20 Bee Brook Rd, Washington Depot; 860-868-6633, gwtavern.com).

STAY:

If sipping on local wines is your first order of business, book a room at Hopkins Inn, where you can stay, eat and drink at a hilltop vineyard overlooking Lake Waramaug (22 Hopkins Rd, Warren; 860-868-7295; thehopkinsinn.com)You might also try picturesque Hidden Valley Bed and Breakfast (226 Bee Brook Rd, Washington; 860-868-9401, hiddenvalleyct.com), which is within a short drive to several local vineyards and wineries. If budget’s not an issue, ultra-private Winvian Farm—a celeb favorite—is home to one-of-a-kind themed cottages (think treehouse, helicopter, greenhouse and stable themes) (155 Alain White Rd, Morris; 860-567-9600, winvian.com). Find more Litchfield Hills Bed and Breakfast destinations here.

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EXTRA FALL FUN:

For maximum fall fun, we’d explore the local vineyards like Haight-Brown Vineyard (29 Chestnut Hill Rd, Litchfield; 860-567-4045, haightvineyards.com) or Hopkins Vineyard (25 Hopkins Rd, Warren; 860-868-7954, hopkins vineyard.com), or go for a beer tasting at Kent Falls Brewing Company (33 Camps Rd; 860-398-9645, kentfallsbrewing.com). If stunning views are first on the menu, try scaling the 37-foot stone tower at Haystack Mountain State Park (Rte 272; 860-482-1817, ctvisit.com) or go hiking at beautiful Steep Rock, which offers all kinds of scenic trails (2 Tunnel Rd, Washington Depot; 860-868-9131, steeprockassoc.org). Did we mention Berkshire Balloons in Plainville can take you on a hot air balloon ride (190 Tomlinson Ave #12h, Plainville, 203-250-8441, berkshireballoons.blogspot.com)? Yippee!

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