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Winter Road Trip to These Quaint Towns

Publish Date: 2020-11-20

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.

Millerton

Where to Stay

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 not only from neighboring farms, but from their own as well. 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!

Things To Do

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!

Where To Eat

If you’re looking to explore local spots of Millerton, stroll down Main Street for some tapas at 52 Main. A place to experience ‘Spanish tradition with American flair’ through their flavorful menu featuring items like Braised Chicken Empanadas, Tuna Poke Avocado and Paella. 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. Come hungry and leave satisfied!

Tivoli

Where to Stay

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 3rd through February 10th.

Things To Do

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! Although COVID has put a halt on some of Dutchess’ beloved attractions, stay tuned for future opportunities to get a glimpse into the fantastic works being safely developed, rehearsed, and filmed at Kaatsbaan Cultural Park. 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.    

Where To Eat

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, catty-corner is a local favorite for Mexican staples. Make the short walk to enjoy fresh, authentic dishes accompanied by a margarita at Santa Fe!

Pawling

Where to Stay

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. 

Things To Do

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. 

Where To Eat

For a small town, Pawling is serving up a memorable culinary scene. The pastries at Pawling Bread Co. will leave you craving them time and time again. With classics like croissants and danishes, or a twist of seasonal ingredients combinations to make your palette dance. 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. 

Millbrook

Where to Stay

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.

Things To Do

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! 

Where To Eat

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

Where to Stay

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 Beacon Hotel’s city feel, 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!

Things To Do

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 Mount Beacon, 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.

Where To Eat

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.

Rhinebeck

Where to Stay

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 newest accommodations. You can't go wrong with either - one offering histric charm, and the other a luxury experience in the heart of this quaint town.

Things To Do

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! 

Where To Eat

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.

For more ideas while planning your trip to Dutchess County, view our 'Plan Your Winter Getaway' page here.

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