Connecticut’s Quaint B&B Getaways

Connecticut is known for its wooded hills, quaint New England town squares, and excellent bed and breakfasts, often situated in historic homes. This quiet state can make the perfect romantic getaway spot for you and your partner. Every corner of the state has its own charms, and we have curated a list of some of the best places to spend a weekend away from it all at one of these five romantic bed and breakfasts.

New Milford

New Milford is known for its famous green, which dates back to the Revolutionary War. The New Milford Green hosts events throughout the year, ranging from art shows to outdoor markets to movie and concert nights in the summer. Abutting the Green is Bank Street, a shopping district known for its quirky stores. The Bank Street Theatre is a cozy movie house that specializes in family-friendly entertainment, as well as special events like short film festivals and specialty screenings. For a picturesque stay, check out the Homestead Inn. The Homestead was built in 1853, and converted into an inn in 1928. If you are an early riser, be sure not to miss the Elephant’s Trunk Flea Market, where vendors from the entire East Coast come to hawk antiques, collectables, and rare finds.


Mystic, located on the estuary where the Mystic River flows into Long Island Sound, is home to Mystic Seaport. The long maritime history of this one-time boating village is on display at the Mystic Seaport Museum, which features an artist in residence, and a working preservation shipyard, where skilled craftspeople build and restore wooden boats. In the shipyard, you can watch the restoration of the Mayflower II, an exact replica of the original Mayflower of pilgrim-transporting fame. Stay the night at the Whalers Inn, situated in a 125-year-old building located in the middle of downtown Mystic. Take a sunset spin on the sea the next day. Mystic, nautical city that it is, has a several companies that offer cruises, including Argia Mystic Cruises, which will take you out to sea on a three-masted sailing schooner.


No relation to Woodstock, New York, that Upstate town of music-festival legend, Woodstock, Connecticut is a tiny town of fewer than 8,000 people that has maintained its rural character. Fairvue Farms is a family-owned working dairy farm that offers tours by appointment. You can even buy fresh half-gallons of their award-winning milk. To round out the experience, stay at the Bed and Breakfast at Taylor’s Corner. The house was built in 1731, and features working fireplaces in each of its three guest bedrooms. Before you go, you may want to stop by one of the AT&T stores in Connecticut to be sure you have an adapter: wires in old houses can be fussy, and you need to be prepared to be sure your phone doesn’t fry if you try to charge it.

New Canaan

This tony town is famous for its prepster vibe and hedge-fund homes, many of which are notable as marvels of modern architecture. Grace Farms features the River Building, designed by the Tokyo-based architectural firm Sanaa. This sinuous pavillion flows across the landscape to create two pavilions connected by a covered roof that is home to offices and public seating areas. The Grace Farms Foundation also hosts public lectures and luncheons from local and national luminaries. Stay the night at the Roger Sherman Inn, whose restaurant is led by executive chef Francois Kwaku-Dongo. Their seasonally-inspired menu features sea-to-table and farm-to-table specials that showcase local ingredients.

New Hartford

Want to really get away from it all? Stay in New Hartford, a tiny town in northern Connecticut located on the Farmington River. New Hartford is a one-time mill town that is now the providence of parks and farms, with five sites on the National Register of Historic Places. Take a stroll in Pine Meadow, a well-preserved 19th century village featuring several immaculate Victorian homes. These homes include the Chapin Park Bed and Breakfast, a restored Victorian house whose motto is “take time for simple pleasures.” With fishing, canoeing, and bicycle tours all within a five minute walk, New Hartford abides by its reputation as Litchfield County’s quiet corner.

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