Best of...

Guide to Litchfield County

The overriding sense that one gets from visiting Connecticut's Litchfield County is that this is the anti-Hamptons weekend retreat for understated, stylish New Yorkers. (Meryl Streep, Dustin Hoffman and the CEO of Manolo Blahnik are famous residents.) Many of the colonial houses date back to the 18th century and throughout drives you'll spot old barns in various states of dilapidation, complete with peeling paint and sinking roofs. This comfortable, lived-in quality emphasizes the laid-back nature of the region, never mind that the estate could value in the eight-figure range. Unpretentious yet quietly impressive is the overriding quality here.

Where to Stay

Mayflower Grace

: The Mayflower Grace celebrates its surrounding landscape, Connecticut's heritage and its guests' comfort in equal parts. The hotel's service and intimate atmosphere makes the Mayflower a wonderful option for couples' retreat, mother/daughter bonding or a spa-centric girlfriends’ getaway.

Where to Eat

Litchfield County is blessed with multiple excellent eateries. Some favorites include the modern and stylish West Street Grill (43 West St., Litchfield; 860-567-3885), which attracts a younger set and Good News Café (694 Main St. South, Woodbury; (203) 266-4663;, a spot that is popular with weekenders and locals alike for their comfort dishes made with local products. Just down the road from the Mayflower, GW Tavern (20 Bee Brook Rd., Washington Depot; (860) 868-6689; is a more traditional affair, full of dark wood antique furniture and serving heartier dishes like pork chops and chicken pot pie.

For lunch, don't miss Washington Depot's top two spots, The Pantry (5 Titus Rd., Washington Depot; 860-868-0528) and Marty’s (4 Green Hill Rte. 47, Washington Depot; 860-868-1700), also known for its excellent coffee and homemade ice cream and sweet treats. If you venture over to nearby Kent, stop in at Kent Coffee & Chocolate Company (8 North Main St., Kent; 860-927-1445; and pick up sandwiches and homemade sides like coleslaw from J.P. Gifford (12 N. Main St., Kent; 860-592-0200).

What to Do


in Litchfield County is excellent, and trails range from wandering paths to more strenuous endeavors and sections of the Appalachian Trail. Topsmead State Forest is a popular 500-acre area to explore, and taking a scenic drive around Lake Waramaug (just outside New Preston) is strikingly beautiful, especially when the foliage is in full force. The Mayflower staff can provide directions and maps of the area. There is also good fly fishing and canoeing in the proper season on the Housatonic River. The Bantam Cinema (115 Bantam Lake Rd., Bantam; 860-567-1916; is the state's oldest and screens classic movies and makes their own delicious popcorn. Another must-visit is Arethusa Farm (822 Bantam Rd., Bantam; 860-361-6600; is famous for its dairy and products for sale like cheese, ice cream and yogurt.

Where to Shop

For such a rural string of hamlets, the shopping is sophisticated and well-curated. The majority is focused on antique furniture  and home décor (notably in the towns of New Preston and Litchfield). The Hickory Stick Bookshop is charming and independently run, and J. Seitz & Company is a home décor shop offering antique and contemporary furniture and design pieces that lure decorators from all over the world. Other musts are George in Washington Depot for mid-century and globally sourced interior home wares, Pergola in New Preston for garden-inspired finds and Plain Goods for a chic curation of high-end clothing and accessories like leather slippers and vintage Hermes.

More Inspiration

Plan Your Trip With Us

We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities.

Get In Touch
Indagare employees walking up stiars

Enjoy 30 Days On Us!

Start your Self Planner
membership trial today.

Unlock access to 2,000+ first-hand hotel reviews, 300+ Destination Guides and the most up-to-date travel news and inspiration.

Already a member?

Welcome back,
log in to Indagare

Not a member?

Forgot Password

Enter your email and we’ll send you a link to reset your password.

Type the first 3 letters to begin