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Quiet Romantic Getaways to Charming Dutchess County Villages

Publish Date: 2020-01-27

Whether you enjoy exploring the outdoors, or good conversation over a memorable meal, Dutchess offers experiences you and your partner will not soon forget. Conveniently situated halfway between New York City and Albany, Dutchess County is the perfect location for your next romantic getaway!

Pine Plains

A town that exemplifies the best of small-town America, Pine Plains’ namesake are its many pine trees. Rumored to have been a stop on the Underground Railroad, the location of a bootlegging and distilling operation during Prohibition, and home to unique natural attractions like Stissing Mountain and Thompson Pond – this country town is anything but ordinary. Get away from it all for a quiet weekend with your special someone. Stay at the cozy Inn at Pine Plains in a bright and welcoming room with en-suite bath. Bet you haven’t had a continental breakfast this delicious, it’s locally-sourced. Shop Hammertown Barn for one-of-a-kind gifts for yourself and your home. Don’t miss a visit to Taconic Distillery (just a 15-min drive from Pine Plains) to try their handcrafted, award-winning bourbon and rye whiskies made on site. A reflection of their surroundings, Taconic embraces a passion for the outdoors and imprints hunting and fishing on their bottled spirits. Have dinner with your sweetheart at Stissing House, an historic 1782 tavern is one of the country’s oldest and longest operating restaurants, offering farm-fresh Provence-inspired cuisine using local ingredients.


Another quintessential small town in Upstate New York, Millerton’s National Register Main Street Historic District features nineteenth and early twentieth century architecture housing, shops and restaurants. Stay at The Millerton Inn, a boutique hotel in a renovated and restored Victorian home from the 1860s. Stroll the sidewalks with your sweetheart and then warm up at Harney & Sons Millerton Tea Shop. Taste your pick from 250 varieties of tea, blended in their factory down the road. Grab a delicious dinner at Oakhurst Diner, the sweetest retro spot with locally-sourced favorites plus unique dishes for every palate. Then catch a Hollywood flick, art film or documentary screening at The Moviehouse.


The City of Beacon features a picturesque, walkable main street corridor with no shortage of delicious culinary options or immersive artistic experiences. Stay in the charming Inn and Spa at Beacon for a relaxing getaway with your partner. Book a massage with one of their gifted therapists on staff and feel the stress leave your bodies during a soak in the Bullfrog Hydrotherapy Spa. Hand-in-hand with your sweetheart, stroll the expansive Dia:Beacon – a large collection of contemporary art housed in a former Nabisco box printing factory on the banks of the Hudson River. Enjoy the city’s growing craft beverage scene and sip local brews, spirits and more at spots like Hudson Valley Brewery and Denning’s Point Distillery. Make a reservation – dinner for two with a side of waterfall views – at The Roundhouse, which serves seasonal new American and also offers a cozy lounge to enjoy drinks and light fare. This can be a car-less getaway, since Beacon is a Metro-North Railroad Hudson Line stop.


Allow yourself to unwind in quaint and picturesque Pawling – home to the world’s shortest St. Patrick’s Day Parade! Easily accessible off the Metro-North’s Harlem Line, find yourself slowing down and enjoying each moment in the walkable village. Book a room in the center of town at the Station Inn Pawling, where country charm meets modern, sleek accommodations. Start your day with a pop-in at Pawling Bread Co. to indulge in freshly baked pastries, delightful dishes and great coffee. Are you an adventurous duo? Take to the Appalachian Trail or Pawling Nature Reserve for hiking or snowshoeing to take in the scenes of eastern Dutchess. Refuel at Vinny’s Deli – a local favorite featured on the Food Network – with their famous Steak Margarita sandwich. Adapt to a slower pace by spending the afternoon perusing the charming shop lined streets. And see where the night takes you, whether that be a memorable meal at McKinney & Doyle, followed by a quiet evening back at the Inn, or lively night out on the town with your sweety at Daryl’s House.


Rhinebeck is continuously earning titles like ‘Most Picturesque Towns in New York State’, ‘Most Charming Towns’ and ‘Quaint Weekend Getaways’ – and the media is right! This charming, historic town with tree-lined streets is just that – picture perfect. Although it may seem tiny, Rhinebeck packs a punch as a culinary destination, cultural mecca, and outdoor enthusiast playground. Find yourself enjoying the unmatched hospitality at the Olde Rhinebeck Inn. This historic farmhouse is run by two best friends, offering authentic, rustic lodging with modern amenities. Saunter through the village for fabulous shopping at local boutiques like Periwinkles, Hummingbird Jewelers or Paper Trail before dining one of the many restaurants serving seasonal, farm-to-table dishes. The best coffee and pastries in town can be found at Bread Alone Bakery. Dine at Terrapin, a former church turned restaurant serving unbelievable local, organic cuisine. Or find yourself in the stylish setting at The Amsterdam enjoying a next level meal and sipping prohibition-era cocktails. Nothing says relaxing with your sweetie like a trip to the spa – schedule an appointment at the serene Haven Spa or the brand new Spa at Mirbeau. And don’t leave Rhinebeck without grabbing some sweets for the road at Samuel’s Sweet Shop for old-fashioned confections. Or savor the best of the best at Oliver Kita – artisan chocolatier.


Experience country meets luxury in the village of Millbrook. Spend your retreat cozying up at the Blue Barn Bed and Breakfast for a relaxing, one of a kind stay. Venture to Millbrook Vineyards & Winery for a tour and tasting of their award winning Hudson Valley Wines. Be sure to take in the natural beauty and rolling farmland of eastern Dutchess as you make your way back into town. Shop the treasures at local antique stores and darling boutiques. Wind down the evening with dinner at Canoe Hill – offering locally sourced, high-end plates accompanied by craft cocktails or wine. Or transport yourselves to France at the quaint, timeless Café Les Baux, a traditional bistro and local favorite.




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