Places to Celebrate - Anniversary Ideas in Connecticut Last Updated: November 2021

Connecticut is a great place to come to celebrate an anniversary, especially if it’s a special milestone. There’s so much to do, so close, it’s easy to arrange a romantic hotel, dining and activities for a short visit or as part of a longer stay. Check out a few interesting ideas that may require some planning ahead but are sure to be an anniversary celebration to remember.

Be sure to check each location before venturing out as hours may change due to COVID-19.

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Stylish Sojourn

Just a short train ride from NYC, Greenwich is a perfect place for a romantic anniversary celebration. At the stylish DELAMAR Greenwich Harbor, book a room, enjoy amazing food at L’Escale or have a couple’s massage. Located right at the marina, you can arrive by boat or book a harbor cruise. You’re also just a few minutes’ stroll to the boutiques and bistros of downtown Greenwich.

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Second Honeymoon in the Hills

Check into the luxurious Mayflower Inn & Spa in Washington and enjoy a getaway in the picturesque Litchfield Hills region of the state. With a spa, Five-Star restaurant, tennis courts and even a putting green, this idyllic property is nestled in 58 acres of beautifully landscaped gardens and woodlands. In the charming village of Washington, grab breakfast or sweet treat at Cafe on the Green or enjoy a cozy meal and drinks at the historic White Horse Country Pub

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Madly in Love

Craving a beachfront getaway? The Madison Beach Hotel offers boutique-hotel style in a resort located in a prime beachside location on Long Island Sound. Stroll downtown Madison for beachy shops and cafes, being sure not to skip a visit to the renowned RJ Julia Booksellers. Or discover beautiful outdoor art at The Sculpture Mile.

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Connecticut River Romance

Combine a romantic stay for two at the quiet, charming Boardman House B&B in East Haddam with a scenic boat ride on the Connecticut River. Stroll down to the Gelston House for a drink, then take a couples' swing at Fox Hopyard Golf Club and admire the rolling hills, running brooks, and other scenery. At night, see what's playing at the Goodspeed Opera House.

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Ocean Break

Stay in a lighthouse suite at the Saybrook Point Inn Marina & Spa for the ultimate in waterfront luxury. Or rent a vacation home in Old Saybrook, like The Cottage or The Nathanial Clark House for a private celebration for two or ten. Take in a socially distanced show at “the Kate” or browse antiques in the many shops and multi-dealer antique centers.

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Nautical Mood

Start your visit to Mystic with a stay at the historic Whaler’s Inn, now a stylish boutique hotel just steps away from the downtown shops and dining. Take a sail on the Argia to see this quaint port town from the water. Back on land, sample seafood at The Oyster Club, Red 36, or S&P Oyster Co. And pick up a unique reminder of your anniversary celebration of tying the knot at Mystic Knotwork.

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Sumptuous Splurge

If it’s a milestone anniversary, you may want to consider booking one of the one-of-a-kind, distinctively designed cottages at Winvian Farm in Morris. You’re in for a luxurious and memorable stay at this Litchfield Hills property, along with five-star dining, a spa and nature center that make any special occasion even more extraordinary. Not far from Winvian, you can visit the home of the famous White Flower Farm garden company. Or take a stroll through the scenic nature preserves of White Memorial Foundation.