Guide to the Litchfield Hills: Things to Do, See, Eat & Stay

Panning a fall escape to Connecticut’s Litchfield Hills? From scenic trails and waterfalls to charming town centers, farm stands, antiques, and standout restaurants, there’s plenty to discover along the region’s winding back roads. Use our guide to find the best places to see, eat, shop, and stay—and start planning your own Litchfield Hills getaway.

Guide to the Litchfield Hills

Litchfield Hills Attractions

Averill Farm, Washington Depot

Get your fill of all the tastes of fall—apples, cider, cider doughnuts—at this 10th-generation family orchard.

Cornwall Covered Bridge, West Cornwall

A favorite subject for photographers, one of the last covered bridges in the state spans 172 feet over the Housatonic River.

Eric Sloane Museum & Kent Iron Furnace, Kent

View artist and author Eric Sloane’s collection of early American hand tools, and study his artwork and his paint-spattered easel in his re-created studio. There’s also a historic iron furnace on-site. Facebook

Kent Falls State Park, Kent

If you’re looking for a short walk with stunning views, try the nearly 1-mile out-and-back Kent Falls Steps Trail, which takes you through a covered bridge to a 250-foot cascade. Picnic tables make this an ideal spot for a family gathering.

Mohawk Mountain, Cornwall

Panoramic views greet hikers and drivers atop Mohawk’s accessible summit.

White Memorial Conservation Center, Litchfield

Four thousand protected acres, including extensive trails for hiking, biking, and horseback riding, are ripe for exploring. Don’t skip the Nature Museum, which tells the story of this vital wildlife sanctuary.

Litchfield Hills Dining

Arethusa al Tavolo, Bantam

The fine-dining star in Arethusa Farm’s food ventures, this local-centric restaurant is inspired by flavors from its home turf. Be sure to stop by the neighboring dairy bar for ice cream.

Community Table, New Preston

Don’t let the casualness of this bistro deceive you: Some of the best food in the region is served right here. Monday’s “Burger Night” is always worth a trip.

Hopkins Vineyard, Warren

Thanks to its next-door neighbor, Lake Waramaug, Hopkins Vineyard enjoys a special microclimate that extends its growing season and nurtures grapes that normally falter in the Northeast. The views aren’t bad, either.

Kent Falls Brewing Co., Kent

Connecticut’s first farm brewery, Kent Falls grows its own hops on land that has been continuously farmed for more than 250 years. Stop by the taproom—the beautiful setting itself is intoxicating.

Warren General Store, Warren

Hard-to-find gourmet delicacies and stick-to-your-ribs sandwiches are all on offer at this downtown gathering spot.

Wilson’s by High Watch, Kent

The good vibes—and the excellent coffee—flow from a deeper mission: Wilson’s was founded by the adjacent High Watch Recovery Center and employs its alumni as part of their reentry into sober life.

Litchfield Hills Shopping

Jeffrey Tillou Antiques, Litchfield

In a region beloved for its antiquing scene, Tillou stands out, with three expansive floors of 18th- and 19th-century Americana right on Litchfield’s famous town green.

Lakeville Books & Stationery, Lakeville

While the cooking section is impressively deep, books of all flavors are celebrated at this Main Street store, opened in 2025 by a family with long-standing local ties.

Milton Market, Litchfield

Tucked away in charming Cobble Court, a former 19th-century livery stable, Milton Market offers a range of home and personal accessories smartly curated by owner Martha Fish.

RT Facts Design & Antiques, Kent

RT Facts’ beautiful showroom runs 7,000 square feet, and its foot traffic has included Martha Stewart and Shonda Rhimes, among other celebs.

Workshop, Litchfield

Since opening her shop in 1970 as a 19-year-old, owner Janus Nelson has become a regional style guru of women’s high fashion, carrying brands like Bryn Walker and Issey Miyake.

Wright’s Barn & Café, Torrington

Antiques and other collectibles, freshly baked goods, and plenty of groovy tunes are all part of the welcoming scene inside this retired dairy barn.

Litchfield Hills Lodging

The Abner Hotel, Litchfield

Even though some of the accommodations are set in former judge’s chambers, there’s nothing stodgy about this courthouse turned hotel. The on-site restaurant is a hub of conviviality, while the rooftop bar will have you deliberating over which well-crafted cocktail to swizzle.

Belden House & Mews, Litchfield

Set on three acres among the historic mansions of North Street, the recently opened Belden marries its main building’s historic heritage with plenty of upscale panache.

Fife ’n Drum, Kent

This homey inn comprises 10 moderately priced rooms on two floors. Decor varies, but all have been comfortably and thoughtfully furnished.

Lost Fox Inn, Litchfield

A compound of three vintage buildings—including a tavern dating to 1745—Lost Fox Inn offers about a dozen boutique rooms and a highly rated in-house restaurant.

Mayflower Inn & Spa, Washington

Amid 58 acres of landscaped gardens and woodlands, this Auberge Resorts property delivers the full luxury treatment: spa, fine dining, and rooms that are both grand and comfortable.

Winvian, Morris

Just a few miles south of Litchfield and adjacent to the White Memorial Conservation Center, this posh rural retreat touts some of the most unusual accommodations in New England: 18 themed cottages, including a treehouse and a beaver lodge.

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