The Hudson Valley’s easygoing highways and scenic backroads have practically become destinations in themselves. Whether covered in wildflowers in the summer or ablaze in gold and auburn in the fall, it’s hard to find a town in the region that isn’t worth a stop. But most travelers, especially those coming from New York City, rarely venture north of the cities of Kingston and Hudson. Those who don’t are missing some of the coolest parts, including growing, under-the-radar upstate cities and towns.
The Hudson Valley covers 10 counties and extends from Yonkers in the south all the way up to Albany in the north. The Lower Hudson Valley consists of Rockland and Westchester counties. The Mid-Hudson Valley, the most popular portion for New York City weekenders, thanks to easy access along the commuter rail, includes Ulster, Dutchess, Orange, and Putnam counties. Many guidebooks and publications focus on these two sections of the Hudson Valley; some even consider them to be the entire valley.
As a 25-year resident of the Upper Hudson Valley, I’d like to put that misconception to bed and show you some of the best reasons to visit.
The often-overlooked Upper Hudson Valley takes the rolling landscapes of its southern sisters and kicks them up a few notches. Within the borders of Greene, Columbia, Rensselaer, and Albany counties, you’ll find the Catskill and Taconic mountain ranges, the beginnings of the Erie and Champlain canals, miles of wild eastern deciduous forest, and dramatic landscapes that frame the Hudson River — the same panoramas that provided the inspiration for the Hudson River School of painting. It’s also home to fantastic outdoor recreation, a growing food and beverage scene, and a number of unique cultural venues.
A tiny hamlet in the town of Shandaken, Phoenicia is situated in a “triangle” formed by the bases of Mount Tremper, Romer Mountain, and Sheridan Mountain. But don’t let its diminutive size fool you. Phoenicia packs a number of sights and activities, including summer music and art festivals, within less than 1 square mile.
The village has several scenic hikes, from simple strolls to challenging clambers. The best are on Mount Tremper and Mount Tobias. In warmer seasons, go fishing or tubing on the Esopus Creek, or push pedals on a Rail Explorers tour.
In the small downtown, take in a show at the year-round Phoenicia Playhouse. You can also visit a handful of shops and galleries, and stop for lunch or dinner. The adorable Phoenicia Diner gets just praise, but it’s often jammed with tourists. I prefer the slower pace of Danielle’s Pizza Shop — a standout in a region where great pie is hard to come by. Follow up with a pint at Woodstock Brewing or dessert at artisan bakery Maeve’s Place.
You may have heard of Windham Mountain, one of the upstate’s premier skiing and snowboarding destinations, with 1,600 vertical feet over more than a dozen trails. In the summer, the resort opens its 18-hole golf course and adrenaline-pumping downhill bike trails.
But that’s not all there is to do in this historic town, which dates back to 1798. Go hiking, biking, or cross-country skiing at Elm Ridge Wild Forest; the lower trails are the easiest. In the downtown, between independent boutiques on Main Street, stop at Windham Fine Arts to browse the gallery or pick up original art for your home. You can also book a facial, using organic products, at the Windham Spa.
Windham has several restaurants to choose from for lunch and dinner. My picks: fresh, unfussy foods at The Windham Local, and wine-focused dining at Ze Windham Wine Bar. The latter features an expertly curated list of 100 international wines, light bites, and cheese and charcuterie plates. In warmer months, enjoy your selections in the lantern-lit Sommelier’s Secret Garden.
Once a powerhouse of shipbuilding, brick making, and ice harvesting (a popular occupation in the Hudson Valley pre-refrigeration), Athens overlooks the west bank of the Hudson River. The 2005 film adaptation of H. G. Wells’s War of the Worlds used a couple locations in town, including the famous ferry scene, shot on the Hudson.
Filled with old Victorians, brownstones, and Italianate architecture, Athens is now home to an eclectic community. Artists, artisans, and small-business owners are leading the town’s resurgence. Visit the Athens Cultural Center, an exhibition and performance space, which also offers live classes, on Second Street. Only steps away, on both Second and Water streets, are a group of shops and eateries. Don’t miss Bonfiglio & Bread, purveyor of excellent baked goods.
The Athens Riverfront Park is a great spot for a picnic, or simply relaxing with a view of the Hudson. In the summer, take a tour of the Second Empire-style Hudson Athens Lighthouse, or visit the annual street fair. Take a load off with one of a dozen beers on tap, plus light bites and sandwiches, at rustic-chic Crossroads Brewing Company.
Cultured Kinderhook is one of the oldest towns in the Hudson Valley, founded by Dutch settlers in the early 1600s. Vestiges of its long history have been left behind in an impressive range of historic buildings, including a Dutch farmhouse where notorious traitor Benedict Arnold once holed up while recovering from wounds sustained in the Revolutionary War.
Start with a walk along the Albany Hudson Electric Trail, part of the newly opened, 750-mile, fully accessible Empire State Trail. Near the trailhead in the village, pause to appreciate the Persons of Color Cemetery, where an estimated 500 free and enslaved Blacks are buried — on just one-quarter acre of land.
Plan to spend a couple hours at the massive The School | Jack Shainman Gallery. Located in a repurposed elementary school, this 30,000-square-foot gallery is one of the best places in New York — including the city itself — to view provocative contemporary art. Then walk down the street for a quick shopping-and-sipping trip, including at the newly opened Kinderhook Knitting Mill. It houses a specialty coffee and retail shop, a home goods boutique, a soda counter, a perfumier, and a wine shop. Have lunch at The Aviary, the new Southeast Asian restaurant from Manhattan chef Hannah Wong.
Pro Tip: The upper Hudson Valley has such a wide variety of outdoor recreation and cultural stops that you’ll want to pack for all contingencies. Bring sturdy walking shoes, plus hiking boots, if you’re planning to hit the trails, and a nice-casual outfit for dining. Also, pack lots of layers. Daytime temperatures can be 30 degrees warmer than nighttime ones, and you’ll appreciate the ability to warm up or cool down as needed.
On the drive into Philmont, you might wonder what there could be to see and do in this quiet former railroad town. Then you turn onto Main Street. Tucked within its handful of shops and cafes is one of the most sophisticated restaurants you’ll find in the region. Local 111, in a repurposed service station, draws diners from near and far to sample farm-to-table cuisine that highlights the rich bounty of the Hudson Valley.
Since the restaurant is only open for dinner, plan your activities around it. Kick off your visit with another exciting surprise: High Falls Conservation Area, where an easy walking trail, through shrouded hemlock ravines, stops at a dramatic 150-foot waterfall. The lower, streamside trail also has mini falls. Or for a more meditative experience, walk the curving lines of the Philmont Labyrinth, a 42-foot, maze-like design on Maple Avenue, on the Village Green. Strolling its stone-lined paths is said to encourage deep contemplation.
Fancy an overnight stay, where you can savor wine and sunsets over Summit Lake? Gather a group of friends and book the Vanderbilt Lakeside, a historic railroad house reimagined as a boutique inn, complete with Manhattan-club-meets-mountainside-lodge decor.
Not a town but a city of 50,000 and the seat of Rensselaer County, Troy is urban energy and convenience in an easy-to-navigate package. It has long been home to a variety of minority and historically disadvantaged communities. Through the guidance of a new group of entrepreneurs, city officials, and artists, the city is undertaking a variety of revitalization efforts.
There’s a reason movies like The Age of Innocence and the new HBO series The Gilded Age were filmed in Troy: its density of well-preserved Victorian architecture provides loads of eye candy, especially on and around River Street.
Catch a concert at the Troy Savings Bank Music Hall, renowned for both its historic architecture and its acoustics. Visit the Arts Center of the Capital Region for an exhibit of local work. Hit the Troy Waterfront Farmers Market, one of the largest and oldest in the region, or hop on the riverside Uncle Sam Bike Trail.
In the downtown, shop for vintage clothing, specialty and imported foods, New Age books, and accessories, home goods, jewelry, stationery, and more. When it’s time to dine, you’ll find upwards of 20 individual options representing a range of cooking styles, plus the new River Street Market, an eclectic food hall. My top picks: Muza for Polish and German favorites like pierogi and schnitzel, and Tara Kitchen for memorable Moroccan food. Prefer not to limit your options? Book a Taste of Troy Food Tour, which mixes city history with local gastronomy at several stops throughout the city.
Pro Tip: On-street parking and public lots are plentiful in most of these towns. The exception is Troy. Attempting to find on-street parking can be a headache here, so locate a garage, public lot, or metered street in advance.
More information about upstate New York is in these TravelAwaits articles: