Embark on a road trip through the breathtaking Hudson Valley

Spanning over 7,000 square miles of mountains, rivers, forests, and farmlands adorned with charming villages and luxurious estates, the Hudson Valley is expansive enough to necessitate a car for exploration.

In contrast to nearby NYC, public transportation options are limited across the region. While buses and trains connect larger towns, driving is essential to access some of the Hudson Valley’s top hikes, historic sites, and quaint hamlets.

Fortunately, the roads here are a dream for drivers. With well-kept parkways and scenic byways, you can enjoy a smooth journey to Albany—just be mindful of a few things. Animal crossings are frequent from dawn to dusk, traffic can back up in Westchester as weekend visitors return to Manhattan on Sundays, winter storms may lead to icy roads, and summer holidays can attract large crowds.

However, don’t let these factors stop you from hitting the road—the Hudson Valley is a year-round paradise. Get behind the wheel and experience it for yourself with these six captivating road trips.

1. Drive along the Taconic State Parkway to witness New York’s shifting landscapes 

White Plains–Chatham; 105 miles

When Franklin Delano Roosevelt envisioned the Taconic State Parkway in the 1920s, he dreamed of a picturesque route allowing city dwellers to escape to the eastern Hudson Valley.

The journey showcases New York's diverse identities, from the bustling streets of White Plains to the rolling hills of the Hudson Highlands and the pastoral landscapes of Columbia County. This parkway, recognized on the National Register of Historic Places, is a delight for road trippers: winding stretches blend seamlessly with the scenery, while charming towns and state parks provide inviting pit stops. 

Be cautious of state troopers – speeding is common on the parkway, and officers are quick to issue tickets. 

The adventure begins where the Bronx River Parkway concludes, transforming the suburbs into Fahnestock State Park within half an hour – a vast 14,000-acre wilderness filled with hiking trails. For an FDR-themed detour, venture 20 minutes east to the former president's estate in Hyde Park, his birthplace and final resting place. 

As the road heads north, public green spaces abound, but Lake Taghkanic State Park, with its 168-acre swimming area, stands out as a top spot for summer outings. The toll-free parkway can be traversed in about two hours, allowing for half a day to explore local attractions. 

2. The west side of the Hudson River offers a picturesque drive perfect for art enthusiasts.

Nyack to Kingston; 71 miles 

Travel along Route 9W, which traces the Hudson River's western edge, leading you through artistic communities and historic towns. Although the drive takes less than two hours, set aside a full day to soak in the sights. 

Your first significant stop is Nyack, the birthplace of artist Edward Hopper (Nighthawks, 1942). Visit his childhood home to discover the inspiration behind his captivating artworks, then get back on Route 9W, passing Bear Mountain and honoring West Point, America’s oldest continuously occupied military installation. 

Next, divert onto Route 218 (also known as Storm King Highway) for a thrilling stretch of winding roads around Storm King Mountain. The views from the drive are stunning, but nothing compares to the breathtaking panorama awaiting hikers at the summit. 

If you skip hiking Storm King, head straight to the namesake art center – a sprawling 500-acre sculpture garden that integrates large-scale modern artworks into the natural landscape. Marvel at pieces from renowned artists like Richard Serra and Louise Bourgeois before continuing on to Kingston, just an hour further north. 

Founded by Dutch settlers in 1652, Kingston boasts an abundance of historic architecture and charming shops that make it worth an overnight visit. Hotel Kinsley, a stylish boutique hotel spread across four buildings from the 17th to 19th centuries, offers a comfortable place to stay. 

3. Discover the opulent Gilded Age mansions lining the Hudson River’s eastern shore. 

Tarrytown to Hudson; 95 miles 

Long before Brooklyn hipsters transformed the Hudson's east side, the elite of Manhattan established Gilded Age residences along the riverbanks. 

Today, these historic estates form a stunning architectural trail stretching from Westchester to Columbia County. Most of these sites are conveniently located near Route 9, a road that glides through idyllic landscapes and sparks some serious real estate envy. 

Starting the journey is Lyndhurst Mansion, a Gothic Revival gem constructed in 1838 for railroad magnate John Gould. Take a spin around the pristine 67-acre grounds before cruising through Sleepy Hollow, the village immortalized by Washington Irving's tale of the Headless Horseman in the 19th century. 

Perched atop Pocantico Hills, Kykuit is a lavish 40-room summer residence built for oil magnate John D. Rockefeller in 1913, overlooking the village below. 

Continue along Route 9 until you reach Peekskill, then veer off on a scenic detour via Route 202 and Route 9D for breathtaking cliffside views along the Hudson. As the road winds into Cold Spring, the 19th-century Boscobel House and Gardens, adorned in imperial yellow, comes into view. 

Reconnect with Route 9 after passing Wappinger Falls and head north to explore the stunning Vanderbilt Mansion and Staatsburgh State Historic Site—two Beaux-Arts masterpieces crafted by McKim, Mead and White in the late 1890s. 

To wrap up your tour of opulent homes, take Route 9G toward Hudson and make a stop at Olana. This Gothic-Moorish estate was once the residence of Frederic Church, a renowned 19th-century landscape painter who depicted the Hudson Valley as America’s Eden.

The drive itself takes about three hours, but plan for a full day to fully explore several estates. 

4. Enjoy fall colors along Seven Lakes Drive 

Sloatsburg–Perkins Memorial Tower; 20 miles

Driving the full stretch of Seven Lakes Drive takes about 30 minutes without any breaks, but outdoor enthusiasts should plan for a half-day experience. 

In addition to meandering past seven stunning lakes, this route provides access to excellent hiking trails, linking Harriman State Park and Bear Mountain State Park. While it's beautiful any time of year, autumn is particularly spectacular when the lakes mirror the vibrant foliage.

Kick off your journey in Sloatsburg, a quaint village filled with delightful dining options like Village Blend (perfect for coffee and croissants) and Seven Lakes Station (known for craft beers and burgers).  

Lake Sebago, the largest lake in Harriman State Park, is the first to greet you, soon followed by a series of beautiful blue pools. Lake Tiorati, the fifth lake along the way, is particularly popular for its public beach, campsites, and access to the Appalachian Trail. Park by any of the lakes to enjoy a peaceful stroll along their shores, and if you're lucky, you might catch a glimpse of a white-tailed deer nibbling at the water's edge when the crowds are thin.

To conclude your trip, head to Perkins Memorial Tower in Bear Mountain State Park for breathtaking views that stretch all the way to NYC. The road to the lookout is open from April through late November, and even if it’s closed, you can still reach the tower via the Appalachian Trail—an experience not to be missed.

5. Venture to the eastern edge of the Hudson Valley for a charming winter escape 

Pawling–Millbrook–Millerton; 40 miles  

While winter may not be the best time for long road trips, it’s perfect for exploring cozy towns nestled in snowy landscapes. This easy one-hour drive winds through scenic farms and forests, stopping at Pawling, Millbrook, and Millerton—three of the Hudson Valley's most charming hamlets along its eastern border.  

Start your journey on Pawling’s lively Main Street. Pick up a new book at Book Cove, savor a delightful pastry from Dancing Bear Cafe, then head north to Route 55, which runs through the Appalachian Trail. Follow Route 82 as it heads north to Millbrook, parking on Franklin Avenue. Make sure you have space in your trunk for any spontaneous finds—Millbrook's antique shops are perfect for giving your home a cozy makeover.

Route 44 connects Millbrook to Millerton, the Hudson Valley's trendy hotspot for stylish New Yorkers. Plan your visit for the weekend to experience the lively crowds exploring the fashionable shops along Main Street.

Irving Farm serves expertly roasted coffee for aficionados, Westerlind offers high-end outdoor gear and local products, while Oakhurst Diner specializes in comfort food straight from the griddle.

6. Follow the Hudson River on an unforgettable three-day adventure

Nyack–Saugerties–Hudson–Beacon–Tarrytown; 199 miles

Dedicate a weekend to traversing both banks of the Hudson River, marveling at the stunning scenery and uncovering its quirky towns. This round trip involves about four hours of driving—perfect for a day trip—but it’s best enjoyed over a long weekend to truly savor the Hudson Valley experience.

On the first day, embark on a two-hour journey north along Route 9W, passing through Nyack, circling Bear Mountain, and arriving in Kingston. After visiting Four Corners—the only intersection in America where all four buildings date back to before the Revolutionary War—head further north to the charming town of Saugerties.

Hike out to the town’s historic lighthouse, constructed in 1869, where Esopus Creek flows into the Hudson. This lighthouse also serves as a B&B—a picturesque place to spend the night.

On day two, head north to Catskill, then cross the river using the Rip Van Winkle Bridge. Dedicate the day to Hudson, a vibrant area famous for its art galleries, antique shops, and delightful restaurants along Warren Street.

Day three involves driving back down the Hudson via Route 9 to Beacon, a trendy town filled with former Brooklyn residents. Explore the impressive installations at Dia—a repurposed Nabisco factory transformed into a modern art hub—before strolling down Main Street to mingle with the locals.

Conclude your journey by cruising through Hudson Highlands State Park, known for its stunning hikes, and finish in Tarrytown. Your adventure wraps up with Nyack, the starting point, just across the Mario M. Cuomo Bridge.