Nothing beats a holiday weekend in New York’s Hudson Valley, especially when you can add a few days of paid time off to extend your weekend getaway into a longer excursion. You deserve a break, and here in Dutchess County, we have plenty of exciting things to see and do this spring and summer, so stay as long as you like!
Take an extra day to relax and finish a book. Dine at a new restaurant (or an old favorite). Visit a fascinating historic site, see amazing works of art, admire the region’s natural splendor on a hike or bike ride, stop at a farm stand and buy some fresh produce to bring home. The possibilities — and the fun — are endless.
These itineraries feature some only-in-Dutchess events and attractions to help you make the most of your vacation time. Happy travels!
• Dates: Wednesday, May 21–Monday, May 26 (6 days; 3 days of PTO)
• Destination: Hyde Park/Staatsburg
• Wednesday (PTO): Treat yourself to a world-class meal at one of the on-campus restaurants at The Culinary Institute of America (be sure to make reservations far in advance). Get a behind-the-scenes look at The Culinary Institute’s world of cuisine with the CIA Experience public tours (Wednesdays, Fridays and Saturdays).
• Thursday (PTO): Visit world-renowned Japanese sake maker Dassai Blue’s state-of-the-art sake brewery for tours, tastings and shopping (closed Mondays). Each tour is followed by a tasting of Dassai Blue sake, a Junmai Daiginjo-only sake -- the highest level of premium sake -- and a food pairing. If you visit during the week, you’re more likely to see the workers in action in the production rooms. For dinner, enjoy a taste of classic Americana, complete with all-day breakfast options and classic burgers, at Eveready Diner (featured on Food Network’s “Diners, Drive-ins and Dives”).
• Friday (PTO): Immerse yourself in opulence with a tour of either, or both, of Dutchess County’s spectacular Gilded Age mansions overlooking the Hudson River: the Vanderbilt Mansion National Historic Site, and, only a few minutes north, the Mills family mansion at Staatsburgh State Historic Site. Afterward, settle in for a hearty meal with seasonal flair at River & Post, which is in the historic hamlet of Staatsburg.
• Saturday: Witness history come alive as the Great Lawn at the Franklin D. Roosevelt Presidential Library and Museum takes on the appearance of a World War II bivouac complete with military displays and period military vehicles, along with soldiers in battle dress on hand to share their love of history (Saturday and Sunday). Then head inside to the FDR Library and Museum (America’s first presidential library and a bucket-list experience for many visitors), and the Home of FDR National Historic Site (the Eleanor Roosevelt National Historic Site, the only NHS dedicated to a first lady, will open for the season sometime later in the spring).
• Sunday: Schedule a wine tasting at Milea Estate Vineyard and savor the flavors of heirloom grape varietals which were originally bred locally as early as the 1800s. Shop for all sorts of vintage treasures at a handful of antique shops on the Route 9 corridor. Plus, the two-day Barn Star Spring Antiques Show will be held only a short drive away at the Dutchess County Fairgrounds in Rhinebeck (Saturday and Sunday).
• Monday (Memorial Day): Get some fresh air on the final day of your getaway with a gentle hike on the Hyde Park Trail System, which offers 34 miles of scenic trails. Walk from the Home of FDR National Historic Site to the Vanderbilt Mansion for breathtaking Hudson River views. History buffs can take the 1.8-mile Farm Lane trail from FDR's Springwood estate to Eleanor Roosevelt's quaint Val-Kill cottage.
• Nearby hotels: The Inn at Bellefield (right across Route 9 from The Culinary Institute of America); Inn the Woods Bed & Breakfast; Journey Inn Bed & Breakfast; Quality Inn; Roosevelt Inn.
• Dates: Thursday, July 3–Sunday, July 6 (4 days, 1 day of PTO)
• Destination: Poughkeepsie
• Thursday (PTO): What would Independence Day be without fireworks? Take a quick jaunt down Route 9D from Poughkeepsie to Heritage Financial Park in Wappingers Falls and admire the rockets’ red glare a day early with the Hudson Valley Renegades minor league baseball team. The High-A affiliate of the New York Yankees, the Renegades are set to host the Brooklyn Cyclones — a New York Mets affiliate — in a South Atlantic League game at 7:05 p.m. The first 1,000 fans through the gates receive a special Stars & Stripes replica Renegades jersey. After the game, stick around for the Renegades’ mega-fireworks show in honor of America’s 249th birthday. There are plenty of food and beverage options inside the ballpark to satisfy every appetite, from the traditional hot dog and a beer to more elevated fare. Enjoy brews from local favorites Industrial Arts Brewing and Sloop Brewing and canned cocktails from Liquid Fables.
• Friday (Independence Day): There’s no more exciting place to watch a fireworks display than 212 feet above the Hudson River at the Walkway Over the Hudson. A repurposed historic railroad bridge, “The World’s Longest Elevated Pedestrian Bridge” offers panoramic views of the mighty Hudson and its majestic highlands, and when the sun goes down, the City of Poughkeepsie’s July 4 fireworks display light up the night sky over the river with unparalleled splendor. There is free parking available near the Poughkeepsie entrance to the Walkway in Pulaski Park (approximately a quarter mile from the Walkway's Washington Street Stairs entrance). There are endless dining options in Downtown Poughkeepsie, including Farmers & Chefs, a casual American bistro which uses the freshest, in-season locally sourced ingredients in its dishes and is situated almost directly under the Walkway. Or, enjoy a cold beer at Poughkeepsie's only rooftop bar and dining space at Zeus Brewing, where the menu includes pizzas, sandwiches, burgers and hand-tossed salads.
• Saturday: The Frances Lehman Loeb Art Center at Vassar College is open to the public and is one of the best free attractions you can visit in Dutchess County. The Loeb is home to approximately 22,000 works of art spanning from ancient times to the modern day, including paintings, sculptures, drawings, photographs, textiles, and glass and ceramic pieces. You can see paintings by the leading artists of the Hudson River School movement of the mid-1800s, including Thomas Cole and Sanford Robinson Gifford, as well as masterpieces of the 20th century by Georgia O’Keeffe, Henri Matisse, Pablo Picasso and Jackson Pollock. When you get hungry, about a 10-minute walk from The Loeb is The Heartwood at Vassar, the college’s sophisticated new carbon-neutral hotel. Inside The Heartwood is The Salt Line restaurant, which is a warm and welcoming place to meet for a delicious meal made with locally sourced ingredients. There are quite a few dining options in the adjacent Arlington neighborhood of Poughkeepsie, including Meyer’s Olde Dutch for burgers and fries, or Juan Murphy’s, which is an “Irish pub with Mexican grub.”
• Sunday: Swing by the Eastdale Village Farmers Market to pick up some fresh local produce to enjoy when you get home. Eastdale Village is Poughkeepsie’s new live-work-play community that offers great shopping opportunities and an assortment of amazing dining options, from sushi to jambalaya, bagels to macarons, and everything in between. If you’re looking to take a nice, leisurely nature walk, the Vassar College Farm and Ecological Preserve is perfect. Located just south of the college’s campus, its expansive network of marked trails takes visitors past forests, wetlands, streams and ponds.
• Nearby hotels: Alumnae House: The Inn at Vassar College; Best Western Plus: The Inn at the Falls; Courtyard by Marriott; DoubleTree by Hilton; Hampton Inn & Suites by Hilton; The Heartwood at Vassar; Holiday Inn; Holiday Inn Express; Home 2 Suites by Hilton; Homewood Suites by Hilton; Hyatt Place Poughkeepsie/Hudson Valley; Quality Inn; Residence Inn by Marriott.
• Dates: Thursday, June 19–Sunday, June 22 (4 days, 1 day of PTO)
• Destination: Northeastern Dutchess
• Thursday (Juneteenth): Begin your long weekend by taking a vigorous hike with a big payoff at Stissing Mountain in Pine Plains. Once you reach the top of the mountain, catch your breath and muster the gumption to climb the 90-foot Stissing Mountain Fire Tower. With amazing views of Thompson Pond along with the surrounding fields and distant mountains, you’ll be glad you went the distance.
• Friday (PTO): Spend the day strolling and browsing in the quaint Village of Millerton. Pick up a good book (or two) at Oblong Books and explore the world of tea and replenish your supply at the Harney & Sons Tea Shop. There are several great dining options in Millerton, including Willa, where you can enjoy delicious, locally-sourced meals and cocktails in a cozy setting. At night, catch a flick at The Moviehouse, an independent movie theater in Millerton. Or, head south on Route 22 for a few minutes to Amenia and catch a double-feature at Four Brothers Drive-In, where you can play a round of mini-golf, munch on tasty treats from the Grand Shack, and enjoy a slice of vintage Americana.
• Saturday: Enjoy a night at the theater! As part of its Local Produce play-reading series, The Stissing Center for Arts & Culture in Pine Plains presents “The Academy,” which tells the poignant story of the relationship between the director of a prestigious boarding school for Black and Brown girls and the valedictorian of the senior class. Who's the teacher? Who's the student? And does either of them belong in a girls' school? The Local Produce series features plays written by Hudson Valley playwrights and performed by Hudson Valley talent. After the show, book a table at Stissing House, a charming French restaurant where you can treat yourself to an exquisite meal prepared by chef Clare de Boer, a four-time James Beard Award nominee, most recently in 2025 for Best Chef, New York.
• Sunday: In addition to crafting award-winning wines, Millbrook Vineyards and Winery in Millbrook hosts an assortment of fantastic events throughout the year. On this particular Sunday, they will be hosting a BBQ Crew food truck pop-up, so pack a few lawn chairs or blankets and enjoy a picnic down by the pond or on the lawn. Schedule a wine tasting and a tour of one of the Hudson Valley’s most iconic wineries.
• Nearby hotels: Hilltop House Bed & Breakfast (Amenia); Hotel Caravana (Amenia; two refurbished Airstream campers at Four Brothers Drive-In); Inverness Bed & Breakfast at Tower Ridge Farm (Amenia); Troutbeck (Amenia; the site of two early meetings of the NAACP, known as the Amenia Conferences of 1916 and 1933); The Inn at Pine Plains; The Millerton Inn; The Millbrook Inn; Millbrook Country House; Wing’s Castle (Millbrook; overlooks the vineyards at Millbrook Winery); Old Drovers Inn (Dover Plains).
• Dates: Wednesday, July 23–Sunday, July 27 (5 days, 3 days of PTO)
• Destination: Rhinebeck/Red Hook
• Wednesday (PTO): Leave all your worries behind as you begin your long weekend getaway with the “Perfect Date Night” package at Mirbeau Inn & Spa, an old-world chic Parisian-style resort in Rhinebeck that earned a prestigious Four-Star Award from Forbes Travel Guide in 2024. This package includes a pair of day-spa passes (allowing access to all property wellness amenities) plus a three-course dinner for two at Willow.
• Thursday (PTO): Schedule a guided tour of Wilderstein Historic Site in Rhinecliff, the riverfront estate once owned by Margaret (Daisy) Suckley cousin and confidante of President Franklin Delano Roosevelt. This Queen Ann-style mansion features 1888 interiors designed by JB Tiffany and grounds designed by Calvert Vaux. Wilderstein's beautiful 40-acre grounds are open year-round and offer extensive walking trails and Hudson River views. Afterward, slake your thirst at any of the area’s popular craft beverage purveyors. Visit the C. Cassis Tasting Room, located in a colorfully repurposed dairy barn in Rhinebeck, and sip their all-natural liqueur made by hand from Dutchess County black currants (black currants were illegal to grow in the United States for about a century until the ban was overturned in New York State in 2003). Milea Estate Vineyard in Staatsburg offers award-winning wines and spectacular views of their vineyard and the mountains in the distance; their Private Tour & Tasting package is an immersive two-hour experience that includes the tasting of six wines, including barrel samples, at the private cottage, along with a local cheese and charcuterie plate, and seasonal hummus prepared by the Milea culinary team. Low-intervention winemaking is the focus at Rose Hill Farm in Red Hook, which produces ciders, wines and co-ferments (best quality fruit, nothing added, nothing removed); enjoy the tap room and outdoor seating areas or pre-book their immersive, 90-minute, behind-the-scenes tasting and tour, led by one of their cider/wine makers.
• Friday (PTO): Bard College’s annual SummerScape festival features a robust, action-packed, summer-long schedule of musical and theatrical performances in and around the iconic Fisher Center. On this particular Friday, you can experience the gripping drama of Bedrich Smetana’s powerful Czech opera, “Dalibor” in the Sosnoff Theater at 6:30 p.m. Or, head to the Spiegeltent — a circus-tent-like venue hosting all sorts of thought-provoking artistry and unbridled festivity — to see Susanne Bartsch’s risqué cabaret production, “New York, New York!” at 8 p.m. (this performance contains nudity). Earlier in the day, you could head to Bard’s Montgomery Place Campus, an adjacent 380-acre estate overlooking the Hudson River, and walk the grounds and admire the views. And don’t miss Bard’s Hessel Museum of Art, a collection of more than 3,000 works by contemporary artists.
• Saturday: Strap yourself in for some high-flying adventure at the Old Rhinebeck Aerodrome in Red Hook. Every weekend from June through October, the Aerodrome stages antique air shows featuring authentic, fully functioning vintage airplanes. The Saturday "History of Flight" program highlights the Pioneer Era before World War I and the Golden Age of Aviation in the 1920s and 30s. The Sunday air show is the World War I dog-fight spectacular, with a hero or heroine, the villainous Black Baron of Rhinebeck, scenery, pyrotechnics and a World War I tank, along with many antique automobiles. There are usually between 15 and 20 flyable aircraft for each show. You can even book your own flight in an open cockpit biplane and admire the scenic beauty of the Hudson Valley from the sky!
• Sunday: Spend some time strolling and shopping in the quaint and walkable Village of Rhinebeck. There are plenty of great places to grab a bite to eat, including Terrapin, where you will experience the best of farm-to-table dining with a menu featuring local and organic ingredients. Head to the Rhinebeck Farmers Market between 10 a.m. and 2 p.m. to pick up some fresh local fruits and vegetables and other items. A short drive from downtown is the Center for Performing Arts at Rhinebeck, a cozy venue where you can sit up close and watch Up In One Production’s 3 p.m. matinee performance of the Tony Award-winning musical “Gypsy.”
• Nearby hotels: The Baker House Bed & Breakfast (Rhinebeck); Beekman Arms and Delamater Inn (Rhinebeck); Mirbeau Inn & Spa (Rhinebeck); WhistleWood Farm Bed & Breakfast (Rhinebeck); Reclaimed Motel (Red Hook); The Red Hook Country Inn; Hotel Tivoli (Tivoli).
• Dates: Friday, Aug. 29–Monday, Sept. 1 (4 days, 1 day of PTO)
• Destination: Southeastern Dutchess
• Friday (PTO): It’s Labor Day Weekend, the perfect time to enjoy the fruits of your labor! Speaking of fruits, apple-picking season shifts into high gear around this time of year, so start your long weekend at Barton Orchards in Poughquag, one of the Hudson Valley’s premiere pick-your-own destinations. Plus, Barton Orchards will be hosting its annual Sunflower Festival during the last two weekends in August, so your timing couldn’t be better! Pick some delicious fruit, pluck some beautiful blooms, and enjoy loads of family-friendly fun on the farm, including hayrides, a corn maze, the dog park, the petting zoo, live music and more.
• Saturday: The Hudson Valley Hot-Air Balloon Festival at Tymor Park in LaGrangeville has been a Labor Day Weekend staple for more than 30 years. Among the festival favorites are the tethered hot-air balloon rides, full hot-air balloon flights, helicopter rides, fireworks, live music and entertainment, food trucks, a beer and wine tent, local vendors, and a whole bunch of family-friendly activities. Bring a picnic blanket and chairs and watch the action from the designated picnic area.
• Sunday: Hunt for treasures big and small at the Stormville Flea Market, with hundreds of vendors offering antiques, collectibles, furniture, jewelry, toys, artwork, crafts, tools, new and vintage clothes, you name it. As featured on the HGTV show "Flea Market Flip," you can find anything and everything at the Stormville Flea Market, which is celebrating its 55th anniversary this season.
• Monday (Labor Day): Lace up those hiking boots and plot a course on the iconic Appalachian Trail, which meanders through the towns of East Fishkill, Beekman, Pawling and Dover before crossing into Connecticut just off Route 55 in the Hamlet of Wingdale. There are a dozen or so parking areas along the Appalachian Trail route through Dutchess. Or, for a short, gentle hike with a photogenic finish, take a short ride up Route 22 to the Dover Stone Church. You’ll hike a little less than a mile over mostly flat terrain until you come to a stunning metamorphic rock cavern shaped like a church’s cathedral with a waterfall cascading through it. According to local legend, the Dover Stone Church was used as a hideout by Chief Sassacus and a group of warriors from the Pequot tribe during the Pequot War in the 1600s. Nowadays, access to the trail is marked with a sign on the southbound side of Route 22. Parking is available nearby at Dover Elementary School (when school is not in session) and at the shopping plaza at 3156 Route 22 in Dover Plains (when school is in session). And if you like fresh, delicious corn, it doesn’t get any fresher or more delicious than Dykeman Farm corn, which is picked daily and sold in their farm market in Pawling. Be sure to pick some up to enjoy when you get home.
• Nearby hotels: The Station Inn (Pawling); Curry Estate (Hopewell Junction).
• Dates: Friday, Oct. 10–Monday, Oct. 13 (4 days, 1 day of PTO)
• Destination: Beacon
• Friday: Beacon’s Main Street corridor is walkable and trendy, with an assortment of restaurants, shops, art galleries and boutique hotels. It is within walking distance of the Beacon Metro-North train station, so getting there from Westchester and the five boroughs is a snap! There is so much to see and do in Beacon, like admiring amazing works of contemporary art at Dia Beacon. This extraordinary collection of artwork from the 1960s to the present is housed in a former Nabisco box-printing factory and is one of the jewels of Beacon's vibrant arts scene. Among the artwork on long-term view at Dia Beacon is "Shadows" by Andy Warhol, which is a single painting composed of 102 separate canvases. At Happy Valley Arcade Bar, you can play fully functioning vintage arcade game consoles and pinball tables; test your skills in Pac-Man, Frogger, Centipede or Asteroids while you sip a craft brew or a signature cocktail. Head to The Vinyl Room to enjoy tasty tapas and a selection from the curated beverage menu, then browse through their collection of more than 2,500 records and try your luck on their vintage video game consoles. Enjoy local craft beers at the Two Way Brewing Company, Pillow and Oats Brewing, Industrial Arts Brewing Company, or the Hudson Valley Brewery. Satisfy your sweet tooth at Glazed Over Donuts or Five Pennies Creamery. The options are endless!
• Saturday: The fall foliage will set the Hudson highlands ablaze with color, making this the perfect time of year to take a trip to Bannerman Castle on Pollepel Island in the Hudson River. Climb aboard the Estuary Steward tour boat at the Beacon dock (located right next to the Beacon train station) and enjoy a gentle, scenic ride to the island, where you can tour the remains of the Scottish-style castle, which was constructed by military surplus dealer Francis Bannerman to contain his vast inventory in the early 1900s. You’ll learn about a fascinating slice of local history and see breathtaking scenery all in one excursion. In the evening, dine with gorgeous waterfall views at The Roundhouse, an industrial-chic boutique hotel that features a new American restaurant with a focus on seasonal, locally sourced ingredients.
• Sunday: Just a short drive from Beacon in Hopewell Junction, the harvest festivals will be in full swing at Fishkill Farms, where you can pick sustainably grown apples straight from the trees, enjoy wagon rides throughout the orchard, get lost in the corn maze, and listen to live music the courtyard while sipping on a hard cider from the Treasury Cider Bar (so named because the farm’s founder, Henry Morgenthau Jr., served as the Secretary of the Treasury during Franklin D. Roosevelt’s presidency).
• Monday (Indigenous Peoples Day/Columbus Day): Autumn is a magical time of year in the Hudson Valley, a time to get outdoors and explore. It’s the perfect time to hike to the top of Mount Beacon; it’s a challenging hike, but the payoff is worth it with scenic views of the foliage up and down the Hudson Valley. Plus, extend the hike to a nearby fire tower for even more panoramic vistas and, on really clear days, views of New York City and Albany. Or, if you prefer to explore by water, Hudson River Expeditions offers kayak rentals and tours from Long Dock Park.
• Nearby hotels: Beacon Bed & Breakfast; Botsford Briar (Beacon); Chrystie House Bed and Breakfast (Beacon); The Dutchess Inn and Spa (Beacon); The Factory Hotel (Beacon); The Roundhouse (Beacon); Swann Inn of Beacon.
Main image of sunset at Mount Beacon by Regina Soules
