Romantic Weekend in Washington, Connecticut

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Advisor - Jill Albino
Curated By

Jill Albino

  • USA

  • Connecticut

  • Couples Travel

  • Domestic Travel

  • Nature Escapes

  • Slow Travel

  • Weekend Getaways

  • Countryside

  • Romantic

  • Vineyards

Lighthouse in Connecticut
Curator’s statement

Washington, Connecticut, is a beautiful destination close to New York City with great spas, excellent restaurants, and antique shopping. It’s the perfect getaway for romance and relaxation without having to take the plane and head far out. And yet, it’s just far enough from the metropolis that it feels like a country vacation.

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Where to stay in Washington, Connecticut

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Things to do in Washington, Connecticut

Hiking in Connecticut

Washington, Connecticut reminds us of Stars Hollow from “Gilmore Girls'' and is perfect for a weekend getaway or staycation at its lovely inns. Enjoy spa treatments in the hotel and spend your day leisurely at the pool. Opt for private couples massage rooms for romance. If you feel active, there are plenty of yoga, mediation, and HIIT classes. 

Nearby Towns

The Washington Depot is a small town with a vibrant cultural scene. Check out the Hickory Stick Bookshop, The Pantry, and Five James to pick up a good read for the weekend. 

When in New Preston, a  small town located south of Lake Waramaug, check out Plein Goods, Privet House, J. Seitz, Dawn Hill Antiques, The Owl Wine Bar, and others.

Enjoy its fine dining, antique, and boutique stores if you venture out to Woodbury. The Antiques Capital of Connecticut has excellent shops like Farmhouse Antiques, Mill House Antiques, The Hidden Acorn, Wayne Mattox, etc. 

 Litchfield is another charming village with historic buildings and cute stores: Milton Market, R. Derwin Clothiers, CP Farmhouse, etc.


Despite being relatively small, Washington also has plenty of culture to offer. The Hen’s Nest is a contemporary art gallery featuring many Connecticut artisans. The KMR Arts is another gallery that hosts monthly changing exhibitions specializing in fine art photography.

If you’re looking to learn a bit about history, check out the Institute for American Indian Studies, preserving the history and traditions of Native Americans. Book the Wigwam Escape Room in advance. The Gunn Historical Museum is a great place to learn about the history of Washington.


Like every upstate destination, hiking abounds. Head out to the Macricostas Preserve for its meadows and farm fields. The White Memorial Conservation Center features 40 miles of trails like The Wheeler Hill Trail or The Lake Trail. 

Visit a Farm

Call ahead to see what activities are happening at Arethusa Farm, Averill Farm, The Farm, and March Farm. Some farms include horseback riding lessons. 

Vineyards and Distilleries

Spend the afternoon sipping wines or sampling beers at Sunset Meadows Vineyards, Hopkins Vineyards, Hawk Ridge Winery, Litchfield Distillery, and Mine Hill Distillery. Each location is excellent to enjoy some lovely liquid libations. 


Washington, Connecticut, is also a great destination for golfing. Check out the Candlewood Valley Country Club, the Stony Brook Golf Course, and the Fairview Farms Golf Club.

Places to Eat & drink in Washington, Connecticut

Olive Bread Connecticut Travel Guide

Arethusa al tavolo: Chic farm-to-table restaurant with great wines and creative dishes. Don’t forget to order the mini cones dessert featuring homemade ice cream. (Book in advance.)

Bantam Bread: Breakfast/snack destination featuring decadent sweets like Elephant Ears and bread including Kalamata olive sourdough.  

Marty’s Cafe: Breakfast spot serving eggs, wraps, and oatmeal. A cute cozy place that reminds us of Luke’s in “Gilmore Girls.” 

Arethusa Farm: The best homemade ice cream in town. Try the sweet cream chocolate chip! 

West Street Grill: Adorable cafe in New Present with outstanding food. Try the vegan burger!

White Horse Country Pub: Have your dinner under the stars by the waterfall at this location. 

GW Tavern: Romantic riverside restaurant serving all-American classics. 

Advisor - Jill Albino

Travel Advisor

Jill Albino

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