« Back to Spotlights

Plan Date Nights in Dutchess with the Inspiration Finder Arts and Culture Trail

Date Published: February 14, 2023

Valentine's Day is a great reminder to celebrate the ones we love, but it's not the only night of the year for romantic outings! Read on for perfect date night pairings: top-notch Hudson Valley cuisine and unique arts experiences.
Download the Dutchess Tourism Inspiration Finder for deals and discounts at a dozen theaters, art galleries and performance venues in Dutchess County. This FREE mobile passport compiles engaging arts, live performances and cultural experiences—all steps away from dreamy dining options. To download your Inspiration Finder (and see the full list of deals), click here.

Stissing Center performance by Wynton Marsalis Quintet
Wynton Marsalis Quintet at The Stissing Center, Pine Plains; Photo by Todd-Gay

Dinner and a Show

Pine Plains: The Stissing Center – Stissing House

The Stissing Center offers buy one, get one free tickets for their incredible live music performances—making their Inspiration Finder deal a must for date night. Before you take your seats, dine at one of the oldest inns in the country, the Stissing House. Eat by the season, with specials like grilled steelhead trout, venison tartare or a rabbit-tarragon pie—and experience the creativity of chef Clare de Boer.

Poughkeepsie: Revel 32° – Brasserie 292

Check into Revel 32° for 10% off live events—which ranges from concerts and theatrical performances to special dinners and dancing. Just a short stroll away, Brasserie 292 offers diners a romantic atmosphere with red booths, copper tin ceilings and old-world French fare. Escargot, oysters and mussels give way to duck confit, shrimp provencal and other elegant entrees. 

Woman sits at white bar with a cocktail at the corner at hotel tivoli
The Corner at Hotel Tivoli

Annandale/Tivoli: Fisher Center at Bard College – The Corner at Hotel Tivoli

For a modern Mediterranean menu in a cheery environment, reserve a table at The Corner at spend a night at Hotel Tivoli! It's only a few-minute drive from the Fisher Center at Bard College, where renowned musicians and artists peform in a stunning Frank Gehry-designed venue. Your Inspiration Finder passport grants 20% discounts on tickets, presenting the perfect Northern Dutchess getaway. 

Beacon: Howland Cultural Center – Sukhothai

Walking down Main Street, Beacon, the gorgeous Howland Cultural Center surely catches your eye. This 1872 structure houses an art gallery and vibrant performance space. After a visit, take a short stroll over to Sukhothai for traditional Thai cuisine—and a few chef specials with modern twists.

Poughkeepsie: Cunneen-Hackett Arts Center – Zeus Brewing Co.

Take a free guided tour of two historic buildings in the heart of the Queen City at Cunneen-Hackett Arts Center. In the warmer months, score a date on the rooftop of Zeus Brewing Co. Pasta and entree specials alongside creative cocktails make this an ideal spot to enjoy an open-air evening. 

Related: Let the Dutchess Tourism Connection Finder Passport be your Guide to Family Fun 

Two women enjoy red wine at 1915 Wine Cellar Poughkeepsie
1915 Wine Cellar Poughkeepsie

Fine Arts with Fine Foods

Poughkeepsie: Gallery 40 – 1915 Wine Cellar  

Discover the work of emerging artists at Poughkeepsie's Gallery 40. This collaborative gallery showcases local creatives, and hosts specicial performances inside the former atrium of a historic boutique hotel. In the same building,  enjoy a glass of romantic red at 1915 Wine Cellar. In addition to their continent-spanning wine list, this upscale Poughkeepsie spot serves eclectic cheese boards alongside game and foraged ingredients.

Beacon: Dia Beacon – Kitchen Sink Supper Club

Experience Dia Beacon for 20% off with the Inspiration Finder passport. Tour installations by Louise Bourgeois, Dan Flavin and other post-1960s artists in the former Nabisco box-printing factory. After, sit down to a chef’s tasting menu at Kitchen Sink Supper Club—complete with wine and cocktail pairings with every course. Small Brazilian bites at Reserva or waterfall dining at The Roundhouse are both excellent options.

Pizza at Lantern Inn in Wassaic
Photo by The Lantern Inn, Wassaic

Wassaic: Wassaic Project – The Lantern Inn

Step into The Wassaic Project for a wholly unique arts experience. Explore seasonal multimedia exhibits and installations from artists-in-residence across seven floors of a historic grain mill. After encountering engaging contemporary art, partake in a workshop for 15% off with an Inspiration Finder check-in. Plus, cross the street to feast on sourdough pizzas and scratch-made pasta at The Lantern Inn.

Cinnamon platter of Indian appetizers
Cinnamon, Rhinebeck

Meals and Movies

Rhinebeck: Upstate Films – Cinnamon

What’s a more classic combination for date night than dinner and a movie? Rhinebeck’s Upstate Films Starr Cinema sits in the perfect spot for this pairing, as the village features a bevy of tantalizing options. Enjoy elevated Indian staples such as tandoori grilled lamb, korma and tikka masala before diving into the latest arthouse flicks. Save room for one medium popcorn at Upstate Films, courtesy of your Inspiration Finder passport.

Millerton: The Moviehouse – Millerton Inn

The recently revamped Millerton Inn serves eclectic Mediterranean cuisine powered by seasonal, Hudson Valley ingredients. In fact, their own farm produces feta, chèvre and Greek Yogurt. Check into The Moviehouse for a free small popcorn and a screening in an atmospheric 1900s building, where films have played for nearly half a century!

Related: Stay Longer for Less with "Stay in Dutchess" Deals 

« Back to Spotlights