Discover the Hudson Valley. Best towns to explore by car from NYC

Driving is the easiest way to explore Hudson Valley towns. With a rental car, you set your own pace, skip train schedules, and take scenic detours. From Manhattan, head north on I-87 or the Taconic Parkway, both offering stunning Hudson Highlands views.  Even bridge crossings feel like part of the trip, with stops for coffee, farm stands, or a picnic along the way. A car means full freedom for your Hudson Valley getaway.

Ready for the road?

Beacon. Art, galleries, and riverside cafés

Beacon has become one of the Hudson Valley’s most creative towns, where art and small-town charm meet along the river. The star attraction is Dia Beacon, a sprawling contemporary art museum in a converted factory that draws visitors from around the world. Main Street is just as lively, with indie galleries, vintage shops, record stores and plenty of cafés for a relaxed afternoon.

Outdoors, you can hike up Mount Beacon for sweeping Hudson Valley views or head to Long Dock Park for kayaking and riverside picnics. The town also makes a perfect base for exploring nearby breweries and the open-air sculptures at Storm King Art Center just across the river.

Just about an hour’s drive from NYC, Beacon is an easy first stop on a Hudson Valley road trip.

Pro tip: start your visit early, so you can pair a museum morning with a late-afternoon hike before heading farther north.

Cold Spring. A quaint riverside village

A little farther south, the village of Cold Spring feels like stepping into a storybook small town. Perched right on the Hudson, Cold Spring’s Main Street is a row of preserved 19th-century storefronts with antique shops, book stores and cozy cafes. The town has an unmistakably all-American sensibility – after all, Don McLean wrote “American Pie” here.

Cold Spring is postcard-perfect: you can walk to Foundry Dock Park for kayak launches or a picnic with sunset views over Storm King Mountain, or hop on a historic trolley that winds through the town. Antique shops here are legendary; you’ll find everything from vintage décor to hand-blown glass pieces made by local artists.

Cold Spring is just 50 miles from the city, so it’s easy to reach for a day trip by car. 

Pro tip: grab lunch by the river. A relaxed riverside meal with views of the Hudson is the perfect break on your road trip north.

Hudson, NY. Vintage finds and eclectic Culture

Cross into Columbia County and you’ll find Hudson, a historic river port turned stylish getaway. Warren Street, the main drag, is packed with vintage boutiques, artisan workshops and antique shops, making it a treasure trove for collectors and casual browsers alike. The city also shines with farm-to-table restaurants, craft breweries and cozy cafés that draw food lovers from across the region. Cultural stops add depth too: the Hudson waterfront is lined with restored wharves, and nearby Olana, painter Frederic Church’s ornate home, offers sweeping valley views.

Hudson is part antique-hunter’s paradise, part foodie hub, and far removed from NYC’s bustle – which is why many road trippers make it their first Hudson Valley stop.

Rhinebeck. History, shops and farmers Market

Rhinebeck is one of the Hudson Valley’s classic historic villages, with a storybook Main Street lined with stone buildings, boutiques, breweries and lively eateries. You can browse chic shops, enjoy a fresh lunch and then take a stroll through nearby woods.

The village is also famous for its Sunday farmers market, where locals and visitors gather for produce, baked goods and live music. With its mix of colonial charm and modern energy, plus nearby attractions like the Franklin D. Roosevelt home in Hyde Park, Rhinebeck remains a favorite stop for weekend getaways by car.

New Paltz. Trails, gorges and college town energy

Further west, New Paltz is a lively college town with a funky Main Street of boutiques, cafés and bars, all set against the backdrop of the Shawangunk Mountains. The area is an outdoor haven: Mohonk Preserve and Minnewaska State Park offer over 70 miles of trails through forests, cliffs and streams, including the adventurous “Lemon Squeeze” hike with sweeping panoramas.

After time on the trails, the town’s laid-back vibe is perfect for unwinding. You can shop, enjoy a farm-to-table meal, sip local craft beer or explore Historic Huguenot Street with its 17th-century stone houses. Just 90 minutes from NYC, New Paltz blends outdoor adventure with small-town charm – hike in the morning, relax on a sunny patio by evening.

Hudson Valley wineries. Taste and relax

No Hudson Valley road trip would be complete without sampling local wines. The region’s climate, with long summer days and cool nights, is well-suited to vineyards, and dozens of picturesque wineries dot the valley. A few standouts include:

• Benmarl Winery (Marlboro): This is the original Hudson Valley winery and holds New York’s first farm winery license. Perched on bluffs overlooking the river, Benmarl produces classic reds and whites and offers sweeping vineyard views.
• Millbrook Vineyards & Winery (Millbrook): Known for its Dutch-inspired barn tasting room and rolling grounds, Millbrook is as beautiful as it is tasty. Their crisp Tocai Friulano is a favorite, and events like food-truck Fridays make it lively.
• Whitecliff Vineyard (Highland): Family-owned for more than 30 years, Whitecliff is known for quality small-batch wines. Their estate Pinot Noir and Chardonnay are popular choices, and the tasting room has panoramic views across the valley.

Beyond these, you’ll find many more wineries and cider houses. A tasting stop adds a relaxing, scenic pause to your road trip – sip a glass on a porch as the afternoon light warms the hills.

Practical tips for your trip

• Take the scenic route - choose parkways or riverside roads like the Taconic or Route 9 for woodland and river views.
• Plan your stops - leave early to avoid traffic and pause in towns like Beacon or Cold Spring.
• Dine local - farm-to-table spots, cider tastings and riverside picnics are part of the experience.
• Check the calendar - festivals and markets add color but also crowds, so plan ahead.
• Be prepared - gas is sparse on back roads, and cell service can drop, so download maps in advance.
• Travel in comfort - choose a spacious SUV for your road trip, for example you can rent a Cadillac Escalade and enjoy the Hudson Valley with ease.

Conclusion

From Hudson River views to cliffside hikes, the Hudson Valley delivers endless surprises once you escape the city. Having a car is the key: a Hudson Valley road trip from NYC means you can chase every scenic outlook, pop into out-of-the-way villages and linger wherever you like.

Book your ride with Drivo, set your own pace — no train schedules, no limits, just the Hudson Valley waiting to be discovered.