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Romantic Hudson Valley Getaways For Any Relationship Status

Determined to think outside of the candy box this Valentine’s Day but want to avoid the landmines peppering the landscape of the most high-pressure romantic day? We’ve created a map of Hudson Valley romance safe zones that will help you emerge unscathed, no matter your current Facebook relationship status.


Status: About to Pop the Question

Length of Commitment: The Weekend

Destination: Rhinebeck

Rhinebeck is the perfect setting for your fairytale romance. Established in 1688 and perched on hills above the Hudson River, Rhinebeck has a colorful cultural past and a dazzling present with a storybook, small town Main Street, more than 400 homes on the National Register of Historic Places, a bustling arts center, antiques stores, quaint bed and breakfasts and some of the tastiest restaurants in the Northeast. The Beekman Arms, smack in the center of the town’s National Historic District, is the country’s oldest operating inn (since 1766). A perfect place to lodge, guests can eat at the first-floor Tavern, or head across the street to other restaurants, bars, shops and galleries.

Beekman Arms Beekamn Arms Exterior. Photo: Beekman Arms.

Plan to book a tasting at the Millbrook Winery, a 30-minute drive from downtown Rhinebeck, then head back to town for cocktails and a bite at Terrapin, an eclectic American restaurant with Asian and French influences — think shredded duck Bolognese and venison medallions in a juniper demi-glace — in a restored 1825 First Baptist Church. The following morning, grab a quick breakfast at Bread Alone bakery and then, as the day progresses, hit one of the nine grand estates in the area (including the Vanderbilts’ and FDR’s former spreads, located 40 minutes away), and/or watch the sun set on the Poet’s Walk. A ten minute drive from downtown Rhinebeck, Washington Irving supposedly was inspired to write “Rip Van Winkle” upon exploring the Walk’s miles of wooded trails, views of the Hudson River, fields and forests laid out by landscape architect Hans Jacob Ehlers in the 19th century.

Room at Beekman Arms Accommodations at the Old Firehouse at Beekman Arms. Photo: Beekman Arms.
Muffins at Bread Alone Bakery A delicious array of muffins at Bread Alone Bakery. Photo: Bread Alone Bakery.
For a luxurious afternoon respite, the Haven Spa in Rhinebeck offers a phenomenal assortment of massages, facials and body treatments for individuals and couples. Top off the weekend with a final epic dinner at the stunning Culinary Institute of America campus in Hyde Park. The haute French restaurant, Bocuse, offers four-star classic French cuisine re-imagined for the 21st century — black truffle soup with puff pastry and slow-cooked pork belly with pickled baby root vegetables. Reservations are recommended.

Status: Falling Hard and Fast

Length of Commitment: A Luxurious Evening

Destination: Poughkeepsie

If your free time is as limited as your love is bountiful, don’t throw up your hands and run for Godiva. Poughkeepsie offers a kind of Cliffs Notes version of the epic romantic adventure awaiting in Rhinebeck. A bustling college town (with Adelphi, Marist and Vassar), Poughkeepsie is both a cultural hub and a foodie destination. Start off the night by hitting the Bardavon 1869 Opera House — the oldest continuously operating theater in New York with a variety of music, theater and film programs spanning the gamut of genres from classical to contemporary. Or, consider swinging by the Frances Lehman Loeb Art Center at Vassar to check out an exhibit (they are open until 9 pm on Thursdays). After all of that intellectual stimulation, grab a romantic bite at Brasserie 292 for top-notch classic French bistro dishes like duck confit or steak au poivre, or the Artist’s Palate, for beautifully rendered modern takes on old-fashioned classics like lamb loin dusted in wattle seeds with a huckleberry-molasses glaze.

Freshly Made Pasta

Freshly made pasta at Brasserie 292. Photo: Brasserie 292.

Status: On the Fence

Length of Commitment: Afternoon

Destination: Bear Mountain

Not yet sure about the object of your affection? If you want to acknowledge St. Valentine without putting too much pressure on a burgeoning relationship, outdoor recreation is the way to go. Not only will you get your pulses racing, but you might just end up holding hands or catching each other’s fall while skating at the world-class, 17,000 square foot outdoor ice rink at Bear Mountain. Snuggle while looking up at the stars that shine on the vast Catskill State Park. The park also has a hand-painted merry-go-round with 42 hand-carved seats decorated with native animals, from bobcats to skunks. Seal the deal (or not) at Bear Mountain’s Blue Roof Tapas Bar, with a variety of Spanish small plates, from the classic beef short rib empanadas to the more esoteric house-made pork rinds and béarnaise dipping sauce. Skating is $5 and rental is $4. Merry-go-round rides are $1 per person.

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