As fall foliage fades, and crisp temperatures sweep Dutchess County, planning a cozy getaway sounds more and more enticing. Winter is the perfect time to escape, even if it’s within driving distance! Pack the car, unplug, and hit the road for a slower pace on this Winter Road Trip to some of Dutchess’ quaint towns.
Located in the heart of this quaint village is The Millerton Inn. The 11-room boutique hotel features a New American Mediterranean restaurant and Tap Room. Embracing the richness of the Hudson Valley's agricultural offerings, the Inn’s dining room offers a seasonal menu using local ingredients. Truly the perfect option for your visit to Millerton, this hotel embraces the culture of the neighborhood and the ancient bones of the building. Centrally located, it’s so easy to get to any shops, restaurants, theaters, bars, or wherever you may be going by foot. Their friendly staff will make sure you have a memorable stay!
Millerton is the perfect quaint town to slow down and recharge. We recommend warming up with a hot beverage from Irving Farm Coffee House and taking in the sights that surround you. More of a tea drinker? Stock up at Harney and Sons, with seasonal flavors including Peppermint, Gingerbread and Hot Cinnamon Spice! Refresh the mind with some outdoor scenery by taking a brisk stroll or bike ride on the Harlem Valley Rail Trail. Access to the trail is right in the center of town, and provides a peaceful, quiet, traffic-free experience. Or take to the Taconic State Park - Rudd Pond Area for a hike on their extensive trails with spectacular views of the Taconic, Berkshire and Catskill Mountain Ranges. Before you head home, shop local to bring home a piece of Dutchess County with you. Whether that means hunting out treasures at the Millerton Antique Center, Hunter Bee, or Montage Antiques, creating a custom t-shirt at T-Shirt Farm, or browsing the selection at Oblong Books & Music - perfect for holiday shopping or just purchasing something that brings you joy! Catch a flick at The Moviehouse as well!
If you’re looking to explore local spots of Millerton, stroll down Main Street for several options. Keep things casual and quirky at the Oakhurst Diner. The retro-style digs will leave you feeling nostalgic, while the menu has a little something for everyone! With diner classics like a turkey club or meatloaf with mashed potatoes, or modern take with dishes like quinoa bowl or beyond meat vegan burger. Of course, the cafe at Harney and Sons is also a local favorite. Come hungry and leave satisfied!
Hotel Tivoli is your best option for a trip to this northern Dutchess destination. The century-old building is situated in this historic town, that sits along the majestic banks for the Hudson River. Owned by painters Brice and Helen Marden, the property is filled with an eclectic collection of furniture, lighting and art. It’s accompanying restaurant, The Corner, offers a Mediterranean-inspired menu, using local ingredients and imported items. The bar presents a delightful selection of wines and fresh-ingredient cocktails designed by Employees Only in NYC. Please note, the Hotel will be closed January 1 through February 15.
Start your day with a cup o' joe at All That Java - a tiny coffee house concept built on a semi-permanent trailer tucked right behind Hotel Tivoli. Owner Samantha Sapienza grew up locally, and on a visit home after living in Seattle for 15 years, she began to dream of bringing the ‘mobile coffee shop’ to the east coast. After getting a caffeine kick, soak in this small town community and experience its art, culture, and nature. Pop into the Tivoli Artists Gallery to admire art from over 40 artists. Keep up-to-date on their latest monthly exhibits! Connect with nature on the trails at Tivoli Bays Wildlife Management Area, which lead to tranquil Hudson River lookouts. Or make your way up to Clermont State Historic Site - a property with miles of trails and river views that borders Dutchess and Columbia counties.
Related: Top 10 Coffee Shops in Dutchess
For your morning jaunt, grab pastries from Tivoli Bread & Baking with a selection of breads, muffins, sticky buns and more. If you’re not choosing to dine at Hotel Tivoli’s on-site restaurant, Santa Fe is a local favorite for Mexican staples. Make the short walk to enjoy fresh, authentic dishes accompanied by a margarita. Tivoli General is another fantastic option that has something for everyone; early-day menus feature eclectic sandwiches, coffee creations and unique baked goods (think black sesame shortbread or local apple-cheese danish) while everchanging late-night menus offer savory fare. In fact, Chef Roy Choi us a big fan! "This is maybe my favorite town in the world. I'm in Tivoli, New York, and this breakfast sandwich is insane. They make an incredible cortado here," he said on an Instagram reel, while enjoying breakfast at Tivoli General.
Right in the heart of downtown and conveniently located near the Metro-North stop, the Station Inn Pawling is the perfect place for your Pawling getaway. This boutique inn is ‘where country charm meets city-cool accommodations’. The ten rooms offer cozy, comfortable and crispy clean space to unwind.
One of the most notable things to do in Pawling is to hit the Appalachian Trail. Don’t let chilly temperatures stop you! Find yourself trekking out on the boardwalk over the Great Swamp. Continue on to the well-known Cat Rocks viewpoint to take in the surrounding landscape of eastern Dutchess. After breathing in the crisp fresh air, enjoy a slower pace by soaking in all Pawling has to offer. Shop local souvenirs like those at Good Tidings Gift Shop, The Blue Olive or Book Cove.
For a small town, Pawling is serving up a memorable culinary scene. Don’t leave Pawling without indulging in the Steak Margherita Sandwich at Vinny’s Deli - featured on the Food Network! Settle in at McKinney and Doyle, where everything is scratch made using the finest and freshest ingredients. An expansive cocktail list plus a bakery full of fresh-baked desserts make this stop a local favorite. Plus, visit Daryl's House Club for dinner and a show, at an atmospheric venue founded by Daryl Hall of Hall & Oates fame.
Experience a unique stay at Wing’s Castle bed and breakfast. The castle was the brain child of artists Peter and Toni Ann Wing. In 1970 the long illustrious love affair of building a castle began. This enigma is still to this day, 47 years later, under construction. As Toni states, "It has become a live-in art project," and a creation using 80% recycled materials. Come for a visit and be memorized by the museum of antique memorabilia and collectibles. Stay here and hear the rest of the story about how the idea of a castle became a home.
Millbrook is known for is sprawling farms and scenic landscape. Embrace the road trip mentality and cruise the picturesque, winding roads of eastern Dutchess. No trip would be complete without a visit to Millbrook Vineyards & Winery. Established in 1982 on a former dairy farm, Millbrook Vineyards & Winery produces a range of high-quality wines that includes Cabernet Franc, Chardonnay, Pinot Noir, Riesling, and Tocai Friulano. Come for a tasting of their extensive portfolio and take in their beautiful property. Stop by Locust Hill Market to stock up on farm fresh goods. Visit the goats and cows on-site, and take home local meats, cheeses, produce, baked goods and more!
For a cozy, yet gourmet stop, head to Babette’s Kitchen. Right in the heart of town, Babette’s menu consists of seasonal entrees, salads, soups, pastas, and homemade baked goods, including gluten-free, vegan and low sugar options to accommodate special dietary needs. Transport to France at Cafe Les Baux. This classic french bistro features dishes rooted in the flavors of the Brittany Sea and land of Provence, such as Escargot, Les Moules Frites and Croque-Madame. The perfect place to warm up and enjoy the flavors of France.
Beacon has a selection of unique accommodations to choose from - all right on Main Street. From The Roundhouse’s modern amenities and waterfall views, to The Dutchess Inn and Spa's luxurious wellness packages, you’ll love the accessibility to all the Main Street action. Both boutique-style hotels have on-site restaurants featuring American dishes highlighting local ingredients, for those who’d rather hunker down and truly enjoy all their accommodation has to offer!
Beacon’s walkability makes enjoying this river town easy peasy. Do some shopping as you stroll to some of the artisan and locally-owned stores. Keep the relaxation at an all time high by bringing home some goods from Beacon Bath & Bubble. Diversify your winter wardrobe at the adorable Blackbird Attic boutique. Or visit the gorgeous Raven Rose for all your home, beauty and wellness needs. Take to the trails with a crisp walk or hike at popular spots like Madam Brett Park or Scenic Hudson’s Long Dock Park. Whether you choose to seek river views or a heart pumping hike, both allow an opportunity to soak in the city of Beacon’s scenic beauty.
Beacon is bustling with mouthwatering restaurants and cafés. What’s better than a hearty breakfast to start your day? Beacon Bread Company offers delicious dishes like chicken and waffles, french toast and classic pancakes. More comfortable dining outdoors? Try Melzingah Tap House! Kick back with a delicious draft accompanied by seasonal culinary creations. Or make a reservation at Café Amacord where you’ll find New American fare in a warm, urban space.
A historic stay in the village of Rhinebeck means only one place - Beekman Arms & Delamater Inn! Coined "the oldest inn in America", the Beekman Arms has been operating since before the Civil War, and retains much of its colonial character, while offering modern conveniences. On the other end of the spectrum is Mirbeau Inn & Spa, one of Dutchess County's most luxurious and restorative accommodations. You can't go wrong with either - one offering histric charm, and the other a winter spa experience in the heart of this quaint town.
The streets of Rhinebeck are nothing short of those out of a movie scene. Adorable sidewalks lined with trees wrapped in lights and locally-owned shops and restaurants. Satisfy your sweet tooth, or warm up with some of the famous hot chocolate at Samuel's Sweet Shop. This must-stop spot is known for its affiliation with stars Paul Rudd, Hilarie Burton and Jeffrey Dean Morgan!
You can't go wrong at any of Rhinebeck's local spots. Dine on contemporary Italian cuisine at Market St., a hot spot with a wood-burning oven and craft cocktails; and still offering a heated outoor patio! Craving a juicy burger? Buns Burgers is the ultimate place to fill up on burgers, hand cut fries and milkshakes that feature local dairy. Be sure to ask for the Buns Sauce and you can thank us later! What's the perfect dish to pair with a chilly winter night? Think warm thai curry from aroi Thai. This casual restaurant offers familiar Thai dishes like pad thai noodles, a selection of curries and local wine. There's also Cinnamon, where diners can expect modern, upscale Indian cuisine. Chef Josh Kroner prepares an assortment of delicious dishes at Terrapin, a gorgeous and romantic date night destination.
For more ideas while planning your trip to Dutchess County, view our 'Plan Your Winter Getaway' page here.