Top 5 Fall Day Trips from NYC: Scenic and Cannabis-Friendly Escapes

NYC may be the city that never sleeps, but the state of New York has tons of places for those wanting to take it a little slower. New Yorkers, not just the ones in the city, flee to sweet little towns north, east, and south into New Jersey as soon as the first leaf turns red. You don’t have to go far to enjoy it all: plan in a couple hours by car or a train ride, and you’ve already escaped.

Hudson Valley

If you’re itching for the gold standard of fall day trips from New York City, Hudson Valley is your spot. Just 90 minutes north of the city, the Hudson Valley feels like an entirely different world — a stretch of river towns, winding roads, and color-drenched hillsides that make fall feel cinematic.

For the drivers, the fall foliage is simply gorgeous on your scenic drive up alongside the Hudson River. There’s a reason “leaf peeping” has become popular, and it’s because of the drive to towns like New Paltz and Kingston to the west of the river.

For the carless among us, public transportation is easy to come by throughout the Hudson Valley. The Metro-North out of Grand Central runs to Poughkeepsie and stops at notable towns like Cold Spring along the way.

Don’t miss:

Dia Beacon: A former Nabisco box-printing factory now filled with towering sculptures and sunlight, Dia Beacon is where art and atmosphere blur together.

Storm King Art Center: Spread across 500 acres of open fields, forests, and hills, Storm King is one of the most breathtaking outdoor museums in the country. Massive sculptures rise from the landscape, glowing beautifully as the sun sets behind the mountains.

Beacon Main Street: This small-town dream is under two hours north of the city. It’s lined with vintage shops, record stores, indie boutiques, and cafés. Grab a cider donut from Glazed Over, browse handmade jewelry, and end your afternoon with serene riverside views before heading back to the train.

Olana State Historic Site: The Persian-style home of Frederic Edwin Church, Olana State Historic Site offers sweeping views of the Hudson Valley. The sights here are breathtaking even after the leaves have fallen. The mansion, galleries, and grounds feel timeless — perfect for a reflective November stroll.

Walkway Over the Hudson: This pedestrian bridge spanning the Hudson River offers panoramic views of the valley. Even in late fall, the crisp air and expansive scenery make it a classic Hudson Valley experience.

Our cannabis travel companion recommendation is, naturally, any product from Hudson Cannabis, based in the Hudson Valley on the east side of the river. This local, organic, women-led, employee-owned cultivator is all about growing “good New York weed.”

The Catskills

You knew this list wouldn’t be complete without The Catskills. This mountain area is known for its hikes, as it has more than 30 peaks and waterfalls. Kaaterskill Falls is probably the most photographed one, rising up 260 feet.

But hiking isn’t for everyone, and the Catskills are big — very big. So let’s focus on a few timeless options:

Woodstock. This town shares a name with the iconic, and later infamous, music festival, so naturally, it celebrates art with theater productions, galleries, and live music. Tinker Street and Mill Hill Road are lined with boutiques, creative shops, and cozy restaurants. November brings a quieter charm, making it ideal for strolling and exploring without the crowds.

Bethel Woods Center for the Arts. The site of the original 1969 Woodstock festival is about an hour and a half from the town of Woodstock. Beyond the museum and gift shop, the autumn views of the rolling hills and river valleys are breathtaking.

Phoenicia. Venture a bit further to this small mountain village for a tranquil, off-the-beaten-path feel. With artisan shops galore and the iconic Phoenicia Diner, it’s a perfect pit stop for lunch or coffee after a hike. The Esopus Creek nearby, with trailheads in the Sleepy Hollow Campground, makes for a reflective late-fall walk.

Mohonk Mountain House & Preserve. For a more luxurious or structured option, Mohonk offers historic architecture, hiking trails, and serene lakeside views. It’s an especially relaxing destination when the weather turns crisp, and it’s timelessly photogenic no matter the season.

The cinnamon in Harney Brothers Cannabis’ Spicy Pound Town tea pairs perfectly with a deep breath of crisp mountain air or the warmth of a crackling campfire. Harney Brothers is based in Millerton at the northern tip of Dutchess County, right in the heart of the Hudson Valley.

Long Island’s North Fork

If you want to spend the day in your own Hallmark channel movie (without the family drama), make your way to North Fork. Fall is the perfect time for your personal rom-com situation amid vineyards, farms, and even a beach. It can’t get any more quaint. This trip is among the more driver-friendly locales on our list, so grab a friend with a car, or hop in a rental and make a day of it.

Don’t miss:

Harbes Family Farm – Mattituck. A quintessential Long Island farm experience, Harbes Family Farm has grown from a small farmstand into a sprawling 100-acre agri-tourism destination. Seasonal produce like pumpkins, sweet corn, and tomatoes fill the farmstand, while the on-site vineyard produces award-winning wines. Fun for all ages, the farm offers hayrides, corn mazes, pig races, and more.

Lavender By the Bay. This family-owned farm, with locations in East Marion and Calverton, offers a serene escape on Long Island’s North Fork. Expansive lavender fields stretch across each property, and the farm’s store offers an array of lavender-based goodies. While early summer is peak bloom season, the quiet charm and scenic vistas make it a peaceful late-fall destination as well.

Orient Beach State Park. Located at the eastern tip of the North Fork, Orient Beach State Park’s waterfront, maritime forest, and saltwater marsh offer a variety of outdoor experiences. Even in November, the crisp air and open vistas make it an ideal spot for reflective walks and riverside views.

Our cannabis travel companion recommendation? Hepworth’s Chemdawg vape pairs beautifully with wandering vineyards, visiting farms, and strolling waterfronts.

Sleepy Hollow, New York

Nestled in the Westchester suburbs just north of the Bronx is the town where legends of Halloween literally came to life. Sleepy Hollow, a village just north of Tarrytown, has embraced its identity as the origin of The Legend of Sleepy Hollow, the spooky Halloween tale of a headless horseman who’s sometimes depicted as having a pumpkin for a head. The town puts on fall events throughout the season, so you’re bound to find something fun to do for the day when you go. This trip is easy, too: it’s a quick drive from the city, or take the Metro-North to Tarrytown.

Some of our favorite Sleepy Hollow day trip activities include:

Sleepy Hollow Lighthouse. Take in the Hudson River with public tours at the Sleepy Hollow Lighthouse, located right on the water. The interior and exterior of the light was restored and renovated in 2024, bringing modernity to a relic of history that’s a quick drive from NYC. It’s enlivening to experience amid the cool autumn air blowing over you.

Philipsburg Manor. At the historical landmark Philipsburg Manor, you can tour a colonial manor and trading center from the 18th century. You’ll learn about the sordid history of slavery on the property, including people who contributed substantially to the wealth of the manor’s owners but received none of this wealth. Reflecting on the history of people expressing their humanity amid systems that suppress it is meaningful not just in the fall, but year-round.

Kykuit, the Rockefeller Estate. With 40 rooms and foliage galore, Kykuit is a portal directly into how four generations of the Rockefeller family lived. The views from some of the outdoor areas are comparable to what you’d see at the end of a long hike up a mountain. And with the trees changing color and floating to the ground, fall is the ideal time to take in these stunning sights.

A day trip to Sleepy Hollow is made for some autumn daydreaming. Pair it with a relaxing indica product like Aster’s Le Crème flower to feel extra cozy on your river cruise or while wandering through sleepy streets.

Finger Lakes, NY

The Finger Lakes are the ultimate mix of small-town charm, sweeping waterfront sights, and hidden gems waiting to be explored. It’s an ambitious day trip since it’s four hours from Manhattan, but if you leave early in the morning, it’s doable, or you can make it an overnight stay. It’s worth the trek — late fall in the region is quieter than peak summer, which means fewer crowds and a chance to really savor the scenery.

Don’t miss:

Beak & Skiff Orchard – LaFayette. This family-run orchard is the heartbeat of the Finger Lakes’ apple scene. Beyond cider tastings and picking your own fruit, they also operate scenic lodging right on the property, so you can wake up to orchard views and spend the day exploring cider tastings and seasonal events without ever leaving the farm. Bonus: Beak & Skiff is also the brand behind Ayrloom.

Ithaca. College town charm meets small-town vibes here, with waterfalls, gorges, and independent shops around every corner. Stop by local favorites like Coal Yard Coffee for refreshments, or walk along Cascadilla Gorge. And for your cannabis companion, Ithaca Organics Cannabis Co. is the perfect pick: locally grown, curated, and ready to enhance your Finger Lakes adventures.

Watkins Glen State Park. Famous for its gorge trails and waterfalls, this park is just as magical in late fall when the crowds have thinned and the air is crisp. After a short hike, you’ll be surrounded by dramatic cliffs and rushing water—it’s one of the Finger Lakes’ best photo ops.

Planning your fall day trip

Whether you have your own ride or you’re renting a car for the day, good planning will take you even further. Sometimes, it’s the journey that matters just as much. If you’re taking the shortest route, you may miss out on some spots, so plan your directions intentionally. Maybe you want to stop somewhere along the way for extra fall activities.

Fall is a notoriously short season, so plan to take your trip between September and November. If possible, head out during the week to avoid the city crowds (yes, even outside of Manhattan). Pack with foresight, too. The weather will likely change during the day, so bring layers, layers, and more layers.

While you’re supposed to take in “the moment,” there are two things you always have to respect: nature and the local culture. Animals and humans call these trip-worthy spots home, and neither want you to treat them like a theme park.

Legal considerations: Cannabis use on day trips

Be considerate of your neighbors when consuming cannabis on your day trip. Hotels, private establishments, and events can make their own rules regarding cannabis. Depending on your itinerary, be sure to check their policies before you go.

Keep in mind that you cannot consume cannabis in the following places:

Federal property

In your car, whether parked or moving

Restaurants

Most public parks

You can consume cannabis in private residences and on private property.

You also can’t take cannabis across state lines, even if you’re taking cannabis from one legal consumption state to another. That only matters if this list inspires you to explore a destination like New Jersey or Connecticut. Any cannabis products you buy at a licensed New York dispensary are perfectly legal to transport within the state.

Finally, and most importantly, safety first. Don’t drive after consuming. Take the train, or ask a friend to be the designated driver for your trip.

Now boarding: Fall season

The area around New York City is simply enchanting in the fall. We highly suggest you take a day to play tourist in your own state. The beauty of fall foliage in New York is something not to miss. We have you covered at The Travel Agency for all your trip supplies.