Top 4 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.

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. The Hudson Valley is also home to the epically-named art center Storm King, an impressive and impressively massive sculpture grounds spread across 500 peaceful acres.

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.

We’re fans of Beacon, about an hour north of New York City on the east side of the river. It’s charming, it’s got gorgeous river views, and art rules the whole community. Don’t miss out on Dia Beacon, this museum on the riverfront that’s taken over a former Nabisco box-printing factory. Stroll along Beacon’s Main Street for the most adorable shops selling donuts, local art, jewelry, and home decor. You can get to Beacon by car or train.

If seeing more nature is what’s on your agenda. Fishkill Overlook Falls on a sunny day is like a living oil painting. This spot, a little off I-84, promises the best fall ASMR of river streams and a general wave of relaxation.

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. Once you’ve made your way up any of its famous hiking trails, we suggest taking in the view with a warm cup of tea. The cinnamon in Harney Brothers Pound Town pairs well with a whiff of a deep breath of fresh air or a campfire. Harney Brothers hails from the Hudson Valley area, based in Millerton, at the northern tip of Dutchess County.

The Catskills are big — very big. So let’s focus on just one little spot you may have heard of — Woodstock. Yes, that one. The town still highly celebrates art with theater productions, art studios, and live music. Woodstock’s main blocks, Tinker Street and Mill Hill Road, are full of creative shops and lovely boutiques. The local restaurants have stepped up their game, too. Mexican and Italian cuisines are reigning the menus, but new Asian and experimental vegetarian spots are also popping up.

Bethel Woods Center for the Arts, the actual place of the world-famous 1969 festival, is just an hour and half from the town itself. If you’re feeling up to it, it’s worth the drive. Aside from the never-ending breathtaking fall views, you can visit the museum, pick up gifts at the shop, and of course, catch a concert.

Long Island’s North Fork

If you want to spend the day in your own Hallmark channel (without the family drama), make your way to North Fork. Fall is the perfect time for your personal rom-com situation amongst vineyards, cute farm stands, and even a beach. It can’t get any more quaint.

Let’s start your stay here with Croteaux Vineyards. Sure, there’s the idyllic scene of rows and rows of grapevines, but there are fall treasures abound on this vineyard. A sweet little barn, pumpkin fall garden for tastings, sunset seating — this vineyard has it all for an idyllic day away from the hustle and bustle of the city. Our sommeliers recommend an equally enticing grape, the Grape Ape vape, to pair with your adventure.

If you want to accidentally meet the love of your life while, let’s say, antiquing, White Flowers Farmhouse is the stage for you. And by “love of your life,” we mean the curated pieces you find here. Everything is handpicked and curated in the spirit of ecofriendliness and sustainability. Be sure to say hi to every single pup you see in-store.

This trip is among the more driver-friendly locales on our list, so find a friend with a car or hop in a rental for the day.

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 an easy one, too: it’s a quick drive from the city, or take the Metro-North to Tarrytown.

Planning your fall day trip

Whether you have your own ride or are 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 even outside of Manhattan. Pack with foresight, too. The weather is likely to 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 alike call these trip-worthy spots home, and neither want you to treat them like it’s a theme park.

Legal considerations: Cannabis use on day trips

Be considerate to 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 — if this list inspires you to explore a destination like New Jersey or Connecticut.

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 during 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.