Upstate New York's Best Small Towns for a Weekend Escape

While the Big Apple may get all the glory, seven small towns in upstate New York offer the perfect weekend escape from the hustle and bustle of big city life with their unique blend of history, culture, and natural beauty. Consider Woodstock’s vibrant arts scene, discover New Paltz's rich history, or explore Tarrytown's historic charm with visits to Lyndhurst Mansion and Washington Irving’s Sunnyside. In Rhinebeck, indulge in farm-to-table or hike up Breakneck Ridge in Cold Spring. Each town promises a memorable experience, making the Hudson Valley in New York a perfect weekend getaway.

Woodstock

Take a scenic drive through the mysterious Catskill Mountains in upstate New York, and sooner or later, visitors will discover Woodstock. Renowned for its hippie culture and arts scene, Woodstock's main thoroughfare, Tinker Street, is lined with eclectic shops, including the Woodstock Emporium and Holiday Haus, Happylife Productions, and restaurants like Little Apple Café, Tinker Taco, and the Tinker Street Tavern, which serves cold beer, cocktails, and live music. There’s even a single-screen theater, Tinker Street Cinema, which has been a Woodstock landmark since 1961.

Visit landmarks like the Maverick Concert Hall, a historic music venue, or catch a performance at the Woodstock Playhouse, a landmark theater known for its productions of Broadway musicals, plays, and concerts. Die-hard Woodstock fans won’t want to miss the Bethel Woods Center for the Arts in Bethel, New York, at the National Register Historic Site of the 1969 Woodstock festival. It’s a 1.5-hour drive from Woodstock, but who doesn’t love a road trip? For a weekend escape, book a room at the Hotel Dylan at the base of Overlook Mountain, where each room is named after one of the rock n’ roll greats associated; enjoy swimming in the heated saltwater pool or sitting around fire pits on the lawn.

New Paltz

Ninety minutes outside New York City, New Paltz is a charming town with a vibrant arts scene, outdoor recreation opportunities, and historic landmarks. New Paltz makes a great base camp for outdoor enthusiasts to explore the Minnewaska State Park Preserve, which features numerous waterfalls, pristine lakes, and scenic overlooks of the Hudson Valley below. Enjoy hiking, biking, swimming, and rock climbing amidst the park's rugged landscape. Some trails to explore include the 22-mile Wallkill Valley Rail Trail that winds through the Hudson Valley countryside or the Shawangunk Wine Trail, where people can indulge in wine tasting and vineyard tours of award-winning wines produced in the region.

Experience New Paltz's vibrant cultural scene by booking a visit to coincide with the town’s many events and festivals throughout the year, including the 69th New Paltz Regatta on June 9, 2024, and the 25th annual Woodstock Film Festival held October 15 - 20, 2024. Add a touch of Victorian luxury to the weekend retreat with an overnight stay at the all-inclusive Mohonk Mountain Retreat, tucked in 40,000 acres of protected forests, overlooking a glacial lake. Visitors are encouraged to arrive early to take advantage of the resort’s activities like ax throwing, paddling, swimming in the indoor pool, or wellness classes before check-in.

Tarrytown

Tarrytown is a small town along the eastern bank of the Hudson River. It is known for its historic charm, scenic views of the river, and proximity to landmarks such as the stunning 1838-era Lyndhurst Mansion—a Gothic Revival country house on 67 acres of land; Washington Irving’s Sunnyside—the former home of the famed author of short stories, "The Legend of Sleepy Hollow" and "Rip Van Winkle;" and the Tarrytown Music Hall, one of the oldest theaters in the United States. Consider staying at the Tarrytown House Estate, an upscale hotel that started as an 1840 home known as the King Mansion, within walking distance of the Lyndhurst Mansion.

Stroll along Tarrytown's historic Main Street, which is lined with charming storefronts, historic buildings, and landmarks like the Tarrytown Clock Tower. There are plenty of restaurants and cafés downtown, like the Bagel Emporium, Rivermarket Bar & Kitchen, and Michelin-rated restaurant Mint Premium Food. Or drop by The Tapp for cocktails, mocktails, beer, and pub-style food.

Rhinebeck

With its historic architecture, boutique shops, and farm-to-table dining, Rhinebeck is a picturesque Hudson Valley town once known as the “Parlor of Dutchess County” due to its hospitality and grand country estates built by wealthy New York families. For a romantic weekend for two, there’s no cuter place to stay than the iconic Beekman Arms & Delamater Inn, established in 1766 and one of the oldest continuously operating inns in America. While there, visit the Antique Market behind the hotel, set in a classic two-story barn with over 30 dealers.

Spend a morning checking out Rhinebeck's art galleries, shops like Samuel’s Sweet Shop, and cozy cafés in its charming village center. Then, grab coffee at Bread Alone Bakery or Rhinebeck Bagels. The Rhinebeck Farmers’ Market is held every Sunday from May through December; this year, it is celebrating its 30th season. Visit Ferncliff Forest, a 200-acre preserve with a pond and 12 miles of trails for walking and mountain biking. Hike 0.7 miles to the fire tower and enjoy views of the surrounding Hudson Valley and Hudson kRiver. Aviation enthusiasts won’t want to miss the Old Rhinebeck Aerodrome, which preserves over 80 vintage aircraft in its museum and hosts air shows every Saturday and Sunday from June 5 - October 20, 2024.

Hudson

Hudson is a cultural hub with its thriving arts scene, antique shops, and trendy eateries on the banks of the Hudson River. Visit Olana State Historic Site, the former home and studio of landscape artist Frederic Edwin Church, and admire its stunning Persian-style mansion, landscaped gardens, and panoramic views of the Hudson Valley. Continue learning about the artist with a visit to the historic 1855-era Hudson Opera House (now known as Hudson Hall), where Frederic Church once showed his paintings.

Hudson is a very walkable city, so stroll along Warren and Front Streets, which are its main thoroughfares. Continue exploring the arts scene with visits to the Carrie Haddad Gallery and the Basilica Hudson, a solar-powered, former 1880s industrial factory now hosting music festivals, weekly concerts and art shows, and other community gatherings. For a luxurious retreat, stay in downtown Hudson at The Maker, an award-winning 11-room property with a lounge, all-day café, and restaurant that has morphed into a lifestyle brand. Be sure to look at their Fragrance Cocktail Menu in the lounge to pick up a bottle of their bespoke fragrances.

Saugerties

On the banks of the Hudson River, Saugerties is a quiet small town with charming shops, outdoor adventures, and historic sites, like the Saugerties Lighthouse. Established in 1869 (to replace the original structure damaged by ice in 1835), the lighthouse is a living museum and a lovely bed & breakfast, accessible by a 0.5-mile gentle hike through a nature preserve. For a longer hike, visit the Falling Waters Preserve—a 168-acre tract of land along the Hudson River with picturesque waterfalls, rock ledges, and stunning views of the Catskills. Another must-see outdoor experience is Opus 40, a monumental environmental sculpture park created by artist Harvey Fite, who envisioned the park as a place for visitors to explore and reflect on the relationships between nature, local history, and the arts.

In Saugerties’ quaint town center, Partition Street is where visitors will discover boutique shops, art galleries, and restaurants like Miss Lucy’s Kitchen, which serves brunch, lunch, and dinner; the Brine Barrel Deli, which pays homage to the pickle; and Alleyway Ice Cream, which bills itself as “the world’s smallest and hardest to find ice cream shop.” Saugerties is also the home of one of the premier horse show venues in the United States, HITS-on-the-Hudson, which features world-class riders competing in show jumping, dressage, and other equestrian events from May through September 2024.

Cold Spring

Start your weekend escape in Cold Spring with a challenging but worthwhile 3.7-mile hike to the summit of Breakneck Ridge in Hudson Highlands State Park. Those who don’t mind a bit of rock scrambling can enjoy insane views of the Hudson Valley at the top. After a morning hike, enjoy lunch at Doug’s Pretty Good Pub on Main Street, Riverview, or the Cold Spring Depot, a historic restaurant in a former train depot dating back to the 1890s. Enjoy classic American cuisine, craft beers, and cocktails in a charming setting with views of the Hudson River.

Cold Spring's picturesque downtown area is renowned for antiqueing at shops like the Cold Spring Antique Center, Once Upon a Time Antiques, vintage clothing at Poor George, or outdoor gear at Old Souls. The Cold Spring Apothecary has locally-made health and wellness products, while books are on the menu at independent bookseller Split Rock Books. Plan to stay downtown at the Pig Hill Inn, an 1825 three-story bed and breakfast with nine individually decorated rooms, or the historic Hudson House River Inn, on the waterfront, steps away from the Hudson River.

Plan Your Upstate New York Getaway Today

Escape for a weekend retreat to upstate New York, where tranquility and adventure await. Enjoy visiting eclectic shops, galleries, and live music venues that celebrate creativity and community. Savor farm-to-table dining and explore historic sites transporting people to a bygone era. Outdoor enthusiasts can hike scenic trails, enjoy breathtaking views, and indulge in wine tasting amidst rolling vineyards. Charming bed-and-breakfasts and luxurious inns provide cozy accommodations, ensuring a restful stay. Visitors seeking relaxation or exploration will discover that upstate New York is the ideal destination for a weekend away.