Hudson Valley & Catskill Mountains Road Trip Itinerary: 22 Fun Things To Do

By | Digital Editor
Last Updated: October 11, 2021
22 Things To Do on a Hudson Valley & Catskill Mountains Road Trip

The Hudson Valley & the Catskills have long been a retreat for overwhelmed New Yorkers seeking refuge from big-city chaos. Whether it was families escaping to the Borscht Belt for the summer, artists flocking to like-minded communities, or adventurers seeking whitewater rafting, the Hudson Valley area was a go-to destination.

Today, its accessibility makes it the perfect road trip destination for a day trip, a week trip, or more. For the sake of this travel guide, we’ll be referring to the general area as ‘the Hudson Valley’ with the understanding that mountain towns are technically part of the Catskills.

Although the Hudson Valley is beautiful any time of year, fall is really when it’s at its finest. Take a long weekend to soak in the gorgeous red, orange, and gold leaves and give yourself time for a hike or apple picking. The picturesque villages seem set up just for that autumnal crisp air.

The Hudson Valley and Catskill Mountains make for a perfect and accessible road trip destination. Here, we list 22 exciting things to do in the region, ideal for a day trip, a weekend trip or longer.
Autumn seems synonymous with New York’s Hudson Valley. Image courtesy iStock.

How To Get To The Hudson Valley

Heading north out of the quagmire that is New York, there are numerous routes that go through the Hudson Valley and Catskills. Start with 87, which heads directly north from the Bronx before veering west to cross the Hudson River and then continuing north once again. Or, take the scenic route and drive along Route 9. It’s much older so it passes historic little towns – which also means it can be a lot slower. At some point, make sure to stay on the west side of the Hudson to be able to access towns like Kingston and Woodstock. 87 is the main artery on the west side of the river, with 9W serving local traffic.

RELATED: Hudson Valley Wine Trail Itinerary: Best Wineries, Hotels, Tours & More

Recommended Itinerary for Navigating the Hudson Valley

Our road trip starts by heading north from New York City. Since it’s a large area, we’ll specify whether the following stops are on the east or west side of the Hudson to make the itinerary a bit clearer.

Tarrytown and Sleepy Hollow

Best known as the home of Washington Irving, references from both Sleepy Hollow and Tarrytown litter his works. They’re located on the east side of the Hudson River, just north of New York City in Westchester County.

Take a Hudson River Sightseeing Cruise

Get an on-the-river experience on a 2-hour cruise that leaves from Kingston, New York. Step aboard the Rip Van Winkle, find a comfortable seat and watch the picturesque natural scenery glide by as you listen to engaging narration from your guide. Travel south to Hyde Park, getting views of the Catskill Mountains, sumptuous estates, sleepy villages and historic lighthouses.

Old Dutch Reformed Church

The Dutch were among the first Europeans to live in the area and their influence is still seen today with buildings like this that date back to the 1600s. Pay a visit to Washington Irving, who included this church and burial ground in his famous “Legend of Sleepy Hollow.” Freak yourself out even more by walking over the Headless Horseman Bridge on the grounds.

Take a Private, Beginner Friendly Helicopter Lesson

Yes, you heard that right. You can try flying a helicopter over the beautiful Hudson Valley. Your aerial experience begins not far from New York City in the town of White Plains. Learn basic flying techniques and safety protocols before jumping in a Robinson Helicopter. Experience views of the Atlantic Coast, the Hudson River and New York’s stunning skyline. Your instructor will guide you and allow you to take the controls for yourself. 

Philipsburg Manor

Philipsburg Manor dates back to Dutch colonial days, and now has a meticulously restored gristmill. Preservationists have more recently increased the visibility of enslaved African-Americans who lived and worked the Manor, a rare historical acknowledgment. 


Because the Rockefellers never did anything small, the Kykuit Estate is just as over-the-top as you might expect the richest man in America to demand. The gardens are lovely and worth checking out as well.

RELATED: 22 Ways To Experience “Old School” New York City


About a half-hour north of Tarrytown is Peekskill, also on the east side of the river. Peekskill is the quintessential Hudson Valley village, with quaint shops and small eateries lining the main streets.

Hudson Valley MOCA

The Hudson Valley and surrounding area have long been a source of inspiration and refuge for artists, and the past few decades have seen an influx of appreciation for the modern and the experimental. This museum of contemporary art includes a range of multi-modal installations. Check in advance for special events.

Sculpture Trail

Created by the above-mentioned HVMOCA, the Sculpture Trail is an engaging walk around town that includes a variety of different sculptures. It only adds to the draw of Peekskill itself.

Bear Mountain State Park

Ok, you’ve been in the car long enough – let’s get out and explore! Bear Mountain State Park is over 1,500 acres with 23 trail miles. Hike, ride your bike, or cross-country ski, depending on the season. It’s always a beautiful spot.

Storm King Art Center

Located about a half-hour north of Peekskill and on the west side of the Hudson, Storm King Art Center is an absolute haven. Take as much time as you need to explore the breathtaking collection scattered all over the grounds. It’s an impressive array.

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New Paltz

This college town is home to some lovely old buildings built by Huguenot settlers in the 1700s. In fact, the Huguenots were such an influence that there is indeed a street named after them. It’s worth spending time exploring downtown – which isn’t exactly large so it’s difficult to get lost – for the old stone architecture.

Wallkill Valley Rail Trail

The Rail Trail stretches from Gardiner up to Kingston and one of the trailheads is in New Paltz. Hike as much or as little as you want, but it’s a beautiful little way to step back in time along a former railway. It’s probably easiest to access by the Wallkill River down by Gun Club Road.

Jenkins-Lueken Orchards

This bit of heaven is located just on the outskirts of town and offers berry, apple, and pumpkin picking depending on the season. Apple picking really is the stand-out, with over 500 trees. Supplement your booty at their farm stand before you leave.

Minnewaska State Park Preserve

Although it’s technically not in New Paltz, Minnewaska is one of the biggest draws to the area. The more adventurous go rock climbing on some fairly steep rockfaces, but those of us who stay on the not-so-daring side of life will certainly enjoy this gorgeous state park. Be careful driving there because those hairpin turns are no joke.

Mohonk Mountain House

This regal hotel offers just about every amenity you can imagine, but you don’t have to stay overnight to enjoy them. Day guest passes are available for golfing, hiking, or just grabbing a cocktail and pretending to be the owner. 


Let’s just get this out of the way: This is not where The Concert was held. It was planned by the Woodstock Music & Art Fair and since that was branded all over promotional posters, we have the legacy of the cultural event thought to be held somewhere it was not.  What a world.

All of that said, the townspeople of Woodstock have no problem making the most out of the confusion and you can find Woodstock The concert-branded goods everywhere. Despite all of this, it’s still an adorable town – c’mon, how cute is the name Tinker Street?

Woodstock Drum Circles

Did you really think we’d cover Woodstock without getting all freaky psychedelic on you? Since you’re here, you might as well swab yourself in some tie-dye and bang a gong. The Facebook group is probably the best way to stay informed on drum circles, but they’re almost always held for the full moon.

RELATED: How To Spend a Long Weekend in the Finger Lakes: Wineries, Hotels & Restaurants

Karma Triyana Dharmachakra

When you’ve had your fill of consumerism and have got to get yourself back to that proverbial garden, head up into the mountains on the outskirts of town for some soul-freeing. This Tibetan Buddhist monastery is the North American seat of the Karma Kagyu line of Buddhism. Attend a personal retreat, take a tour, or just shop at the bookstore in these breathtaking grounds.

Town Tinker Tube Rental

Ground yourself back in reality by diving into the mighty Esopus! Located west of Woodstock, stop off at Town Tinker to go tubing down the river. This is not for the faint-of-heart! Class II whitewater can include some adrenaline-spiked waves but it’s the perfect experience for thrill-seekers on hot summer days.


Located on the east side of the Hudson, Rhinebeck is one of the most charming towns around. Dating back to the 1700s, Rhinebeck manages to embrace both the historical and the contemporary with an eclectic mix of shops, restaurants and experiences.

Beekman Arms Delamater Inn

Holding the title of “Oldest inn in the United States”, Beekman Arms has been in operation since 1766. Staying or dining there are both fantastic, but just settling in the tavern for a grog of ale is enough to give you a taste of New York’s early days.

RELATED: 10 Exciting Outdoor Activities in New York’s Finger Lakes Region

Omega Institute

Give yourself the gift of peace and quiet and book an R&R Retreat Weekend at the placid Omega Institute. Drop-in yoga classes and guided meditation are worth it, but even just reading in a hammock for hours is delicious. Omega also offers bodywork, theme weeks, and more. It’s a gem.

Wilderstein Historic Site

If the pared-down décor of Omega isn’t for you, you’ll love the Wilderstein Historic Site. Built-in the mid-1800s, it’s a Queen Anne style mansion that was home to FDR’s cousin/companion Daisy in the later years of her life.

The Hudson Valley and the Catskill Mountains provide endless opportunities to explore nature, adventure, art, and culture. It’s one of the oldest European-settled areas in the country and, although it has had its share of economic hardship over the years, it continues to develop and thrive. If you’re looking for more things to do in the New York area, be sure to browse these other travel guides, book this itinerary or design your own route with Winetraveler.

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