The Loveliest Day Trips From NYC for Food, Culture & the Outdoors

The view at the top of Kaaterskill Falls in fall, one of the best hikes in Upstate New York

New Yorkers! Need a small break from New York City living? Looking for an easy and refreshing New York getaway? Consider one of these wonderful day trips from NYC. From small New York towns to natural wonders – there is so much for us to explore just 1-2 hours from Manhattan. And if you don’t have a car, don’t worry, we’ve also included ways to reach most of these destinations by bus or train. Below are the best day trips from NYC.

Table of Contents

The Best Day Trips from New York City

1. Beacon, New York ★

The town of Beacon, New York is located in the majestic Hudson Highlands, along the Hudson River. In Beacon, just strolling in the downtown area, visitors are greeted with a charming art scene, delicious restaurants, and boutique shops. To give you a feeling of the vibe here, there’s a beautiful book store proudly displaying a “BLACK LIVES MATTER” sign that warms up the street.

Things to Do in Beacon as a Day Trip From NYC

  1. Dia: Beacon Museum: Reserve your tickets ahead of time to visit this museum’s collection of art from the 1960s to the present.
  2. Bannerman Castle: Take a ferry to Pollepel Island to see visit the Bannerman Castle (pictured above) with Bannerman Island Tours.
  3. Go Kayaking: Consider kayaking along the Hudson River with Mountain Top Outfitters. You can also kayak to Bannerman Castle!
  4. Walk down Main Street: Check out the beautiful shops along Main Street. This is a really fun walk that leads you to…
  5. Beacon Waterfall + Roundhouse Restaurant: Get lunch or dinner at the palatial Roundhouse Restaurant overlooking a beautiful waterfall. For a more affordable option, get a cocktail at Roundhouse and then dinner at Melzingah Tap House.

How to Get to Beacon From NYC

  • Train: Beacon is a 90-minute train ride on the Metro-North from Grand Central Station for about $20 each way. From the Beacon train station, you walk to Main Street in 10 minutes.
  • Car: 90 minutes driving north of mid-town Manhattan.

2. Woodstock, New York ★

Hands down, one of the best small New York towns to visit near NYC. Although the town has been famed for the historic Woodstock Festival (which actually took place in Bethel), Woodstock still offers the friendly hippie vibes, a unique art scene, and that charming 60s culture.

The downtown area has several restaurants, shops, and a bookstore that warms up the street with a sign that reads “Black Lives F*cking Matter“. Amen to that. It’s not easy feeling welcomed as a person of color once you leave the city, so signs like this help us feel a little relief.

When I first entered Woodstock, I stumbled upon a circle of drummers playing music, and seconds later one of them invited us to play with them. Woodstock is also a wonderful place to connect with friendly locals.

Things to Do in Woodstock – New York Day Trip

  1. Waterfalls & Hikes: Go hiking in one o the many nearby trails or waterfalls such as Kaaterskill Falls or Fawns Leap. Or, if it the weather permits, jump into one of the natural swimming holes nearby for a refreshing swim.
  2. Downtown Area: Stop at one of the many delicious restaurants in Woodstock. If you like tacos, I recommend Oriole. Woodstock has a ton of charming restaurants from Asian fusion cuisine to restaurants perched along the water with outdoor picnic tables.
  3. Dessert lovers must stop at Sweet Dreams Organic for their ice cream.
  4. Art: Check out art spaces such as Woodstock Artists Association & Museum, the Elena Zang Gallery, and the Woodstock Byrdcliffe Guild.
  5. Shopping: Pop into the town’s many boutique shops and bookstores like The Golden Notebook.

How to Get to Woodstock from NYC

  • Bus: You can take the Trailways bus from Manhattan to Woodstock in about 2 hours for about $30 each way. From here, you could spend the day in town and/or take Ubers for trips to nearby spots.
  • Car: Driving to Woodstock is about 2 hours from Manhattan.

3. Greenport, Long Island ★

This port town is located towards the far end of Long Island’s North Fork; a region renowned for its vineyards/wineries, small farms, restaurants, and flower fields. Best of all? There is an LIRR station there that will take you directly to GREENPORT! One of the best places on the USA East Coast! From here, you can take a ferry from there to Shelter Island (listed as #5 below).

Can’t-Miss Experiences in Greenport, Long Island

  1. Tea Garden: Have high tea in this beautiful garden where you can order beautiful herbal infusions and pastries like biscuits or lavender macaroons.
  2. Downtown Area: Walk through the area to really absorb the vibe of this port town. Check out the boutique shops and antique stores. And/or create your own foodie tour by stopping at one of the many restaurants in town. A must-visit spot is Crabby Jerry’s or Claudio’s (same owners) for their stuff clams!
  3. Ferry Ride to Shelter Island: Take a $2 ferry to Shelter Island – listed below.
  4. Long Island Wine Country: Go to one of the many wineries/vineyards nearby for an afternoon of wine tasting – listed below.
  5. Lavender by the Bay: Buy some of their local lavender honey, stroll through the lavender fields, and stock up on lavender-scented-everything.

How to Get To Greenport From NYC

  • Train: Take the LIRR to Greenport. The station is right in the center of the town. Or, if the schedules don’t align for you, take the LIRR to Ronkonkoma and then an Uber to Greenport (if you’re with friends you can easily split this ride to save on costs).
  • Driving: Or you can drive there in 2 hours from NYC.

4. Shelter Island, Long Island ★

Day trip from NYC to Shelter Island for kayaking and delicious seafood

Shelter Island is special. Not just because it’s lush, quaint, underrated, and located just minutes from Long Island by ferry–but there is also a unique history of Greek and other European immigrants who moved here in the 1900s and have shaped the island’s modern-day ambiance. Today, the island retains a unique multicultural heritage while also being home to some of the most expensive and lavish homes in the country.

Be sure to pair your trip to Shelter Island with a visit to Greenport (listed above).

Things You Can’t Miss on Shelter Island

  1. Rent Bikes: To peddle around the island.
  2. Kayaking: This is one of my favorite places to go kayaking on Long Island! You can rent kayaks here for about $50 per person to see the beautiful bay, stop by a historic home, see the beaches, and other natural wonders.
  3. Mashomack Preserve: 2,000+ acres of a nature reserve with marshes, forest & creeks. Perfect for easy hiking.
  4. Commander Cody’s: This black-owned restaurant serves delicious seafood out of a cozy space that feels like home. Don’t forget to try the fried pickles and cornbread!

5. New Paltz, New York

New Paltz is special. As soon as you enter the town, you’ll see a small Dominican restaurant at the foot of the main street two hours north of NYC. That alone wins major points for this small artistic college town in the Catskills. If you love good food, art, culture, and the outdoors, New Paltz is not just one of the best small towns in New York to visit, but it makes for one of the best day trips from NYC!

New Paltz Top Things to Do – NYC Day Trip

  1. Stroll the downtown area – New Paltz is home to several restaurants and shops in their expansive downtown area. Their restaurant selections range from Turkish to Dominican food! And there are several side streets to explore for art or shopping as well.
  2. Hiking – New Paltz is at the foot of so many different hikes from NYC to choose from. The most popular ones are in Minnewaska State Park Preserve and Mohonk Preserve.
  3. Art – Since New Paltz is home to the college of SUNY NEW Paltz, which specializes in art, you can find several art galleries in town such as DM Weil Art Gallery Unison Art Center.

How to Get to New Paltz

  • Driving: You can drive here from NYC within two hours.
  • Train + Uber: Take the Metro North up to Poughkeepsie and then take an Uber to New Paltz.
  • Bus: Take a 2-hour Trailways bus from Port Authority in Manhattan.

6. Cold Spring, New York ★

This small New York town is one of the easiest NYC day trips because it’s maybe 75 minutes by train from Grand Central. And their train station is right in the downtown area! The perfect NYC getaway to the Hudson Valley.

Easy NYC Day Trip to Cold Spring To Do:

  1. Kayaking & Paddleboarding: Over the Hudson River with Hudson River Expeditions.
  2. Hiking: There are several hikes from Cold Spring such as: Breakneck Ridge, Bull Hill, Cornish Estate, and much more.
  3. Magazzino Italian Art Museum: A must-visit for art and culture lovers. This museum is a gorgeous homage to Italian cultural heritage.
  4. Downtown: The downtown area (pictured above) is full of shops and restaurants to choose from. If you walk all the way down to the river (through the underpass), you can stop by a beautiful open space facing the Hudson River, where you can sit on one of the many benches over a scoop of local ice cream.
  5. Stone Crop Gardens: Beautiful public garden. Book your appointment here.

How to Get to Cold Spring

  • Train: Take the Metro-North just a few stops from Grand Central!
  • Driving: A little over an hour driving from Manhattan.

7. Fruit Picking in Redhook, New York

Redhook is home to several of New York’s farms. Here you can stop by local small farms to buy produce and other foods or to do some fruit picking. Perfect for relaxing in nature or an activity for your family/kids.

Greig Farm is where I went for blueberry picking and apple cider donuts. They also offer a variety of fruit pickings that naturally changes per season.

How to Get to Redhook From NYC

  • CAR – About 2.5 hours driving from NYC.

8. Port Jefferson, Long Island ★

This underrated Long Island town feels a world away from NYC. Here you can visit the waterfront/beach, enjoy watersports, go boutique shopping, pop into the restaurants, and more. But my favorite? Pirate’s Cove (pictured above) – a beautiful sand dune formation with a beautiful beach area at the bottom.

How to Get to Port Jefferson From NYC

  • Train: Take the LIRR to Port Jefferson train station. From there a 5 minute Uber will take you into the town’s center.
  • Driving: Two hours from Brooklyn.

9. Long Island Wine Country ★

Did you know there is a quaint region renowned for its vineyards, wineries, beautiful outdoors, and local markets? On the same island as Brooklyn and Queens? Welcome to Long Island’s North Fork where you can find Long Island Wine Country. You can also combine this trip with a stop at one of the many small towns on Long Island like Greenport, Oyster Bay, and Port Jefferson.

Long Island Wineries to Try on Your Day Trip

  • Shinn Estate Vineyards & Farmhouse – This one is my favorite. Stunning vineyard with high-quality wines and ingredients in a cute and relaxing setting.
  • Pindar Vineyards – Stop by their beautiful sunflower garden
  • Sparkling Pointe
  • Kontokosta Winery

Bonus: Consider stopping by the Hayward Restaurant for dinner. Or dropping into Greenport (listed above) on your trip.

How to Get There From NYC

  • Car: The region expands from Mattituck all the way through around East Marion. So it depends on what part you’d like to go to.
  • LIRR Train + Uber: Google one of the vineyards and take the LIRR to the nearest point and then call an Uber.
  • Bonus: Ubers are a third of the price in Long Island than they are in New York City.

Long Island Winery Tours

  • This wine tasting tour which includes transport to and from NY. You’ll visit 3 different award winning Long Island wineries, and get to sample 10 to 12 different wines. The tour also includes lunch, and a guide. Book here.
  • Bike Tour of Mattituck Farm & Wine Country: On this tour, you’ll join a tour and go cycling through Mattituck and visit a local farm, 2 different vineyards and hang at a beach for extra-virgin olive oil and vinegar tastings. Book here.
  • On this PRIVATE bike tour you’ll spend about 4.5 hours cycling through Mattituck. This includes 2 wine tastings per person, and 1 set of herb infused oil and vinegar tastings. This one is PRIVATE, so it will cost more. Book here.
  • This Long Island Winery Tour visits the Osprey’s Dominion Vineyards and Duck Walk Vineyards. The tour includes 2 different wine tastings, and private transportation within Long Island. Book here.

10. Kingston, New York

The first capital of New York State, Kingston, offers several things to do for a quaint day trip. As one of the battlegrounds during the American Revolution, much of Kingston was burned down by the British. But still, remnants of Dutch and colonial influence can be found well-preserved especially in its historic center.

The city of Kingston is divided into three parts: Uptown, Midtown, and the Rondout (the waterfront). If you can only pick one, I recommend strolling around uptown. Here you can head straight to Rough Draft Bar & Books located in an old colonial-style building on a historic street. And if you’re in Kingston on a weekend, stop by the Kingston Farmers Market.

How to Get to Kingston From NYC

  • Bus: Trailways bus from Port Authority for about $30.
  • Driving: About 2 hours north of NYC by car.

11. Hudson Valley & Catskill Hikes Day Trip Near NYC

OK! So! The Hudson Valley and the Catskills are huge. And there are so many natural wonders and outdoor opportunities to choose from in these regions. But the easiest outdoor thing to do that is usually free? Hiking!

There are hundreds of different hiking trails within 2 hours day trip near NYC. Consider taking a day in nature to enjoy the outdoors while moving your body. A much-needed experience for many of us cooped-up New Yorkers. Here is a full list of our top recommended –> beautiful hikes from NYC. And if you want to go further up-the-state, check out our guide to the best hikes in Upstate NY.

Are you craving a hiking day trip from NYC but don’t want to go alone? I hear ya! Solo hiking can be scary. Here is where this group Catskills hiking tour, by local guide Brian, comes into place. Bonus: You can combine this trip hike with a trip to the cute town of Woodstock (on this list).

12. Go Horseback Riding

When you think of New York, I’m sure horses are one of the last things you imagine. But New York State is home to several horse ranches where you can do a horseback riding lesson or trail tour through the beautiful outdoors. The perfect break from the hustle and bustle of city living while reconnecting with nature and getting a great workout!

13. Storm King Art Center, NY

Storm King Art Center is renowned as one of the world’s leading sculpture parks for 50+ years. Just one hour driving from NYC, this art center offers 500 acres of rolling hills, meadows, and tree-lined woodlands that will make you think you’re in another country.

The combination of natural beauty and stunning modern art makes for the perfect cultural, outdoors, and social distancing experience. This is a must-visit day trip from NYC for art lovers.

This region in the Hudson Valley makes it easy to add other unique experiences into your day trip out of NYC:

  • Go hiking at Stewart State Forest, Schunemunk Mountain State Park, or Storm King Mountain.
  • Visit Angry Orchards cider house.
  • Check out Beacon, NY (listed above).
  • Visit the town of Cornwall-on-Hudson
  • Check out Bannerman Castle
  • Visit one of the many wineries in the region such as the Brotherhood Winery

How to Get To Storm King Art Center From NYC

  • Metro-North + Uber: Take the Metro-North train to Beacon, New York. Then an Uber to the Storm King Art Center.
  • Driving: About 90 minutes north of NYC by car.

14. Visit a Waterhole Like Peekamoose Blue Hole

Peekamoose Blue Hole is a crystalline, emerald-blue, natural swimming pool tucked within the verdant Sundown Wild Forest in the Catskill Forest Preserve. This idyllic blue hole is formed as a part of the Rondout Creek, which flows into the Rondout Reservoir, where nearly half of our drinking water in New York City comes from!

However, today, Peekamoose Blue Hole is at risk of being shut down to the public due to the pollution and environmental strain from the mass crowds visiting every year. So if you do a day trip here, get there during off-peak season and be mindful. Please read these important things to know beforehand so that you can better enjoy your experience while still conserving it.

How to Get To Peekamoose Blue Hole

  • Car: About two hours north of NYC.

15. Montauk, Long Island ★

Montauk is a bit further out. In fact, it’s the farthest point on Long Island. So you’ll have to start your day very early to maximize your time in Montauk, but it is worth it. Montauk is actually one our favorite towns on Long Island to visit. So much so that we dedicated an entire guide to the best things to do in Montauk.

Top Things to Do in Montauk – Day Trip

  1. Hike the State Parks in Montauk – Montauk is home to some of the prettiest New York State Parks and best hiking trails on Long Island! So if you love the outdoors, a hike in Montauk is a must-do.
  2. Check out the Montauk Point Lighthouse
  3. Go Kayaking in Lake Montauk, Fort Pond, or Big Reed Pond.
  4. Take a surfing lesson
  5. Go sailing
  6. Take an e-bike tour
  7. Go beach hopping through some of these beautiful Montauk beaches.

How to Get To Montauk from NYC

  • Bus: Take the Jitney bus which can drop you off in Montauk.
  • LIRR train: Take the Montauk train there. It can take 2.5-3.5 hours. Schedule your commute time wisely.
  • Driving: About 3 hours east of NYC by car.

16. Philadelphia, Pennsylvania

You’re probably wondering: Pennsylvania? Isn’t that super far from NYC? Well actually, the “City of Brotherly Love”, Philadelphia, is just 90 minutes from New York City by train! This underrated city is bustling with significant American history, traditional and modern art, hundreds of hip restaurants, and tax-free shopping; all while being rich and diverse in culture.

Things to do on a Philadelphia Day Trip from NYC

  1. Museums, museums, museums! Philly is home to countless museums. But on a day trip, don’t miss these: The Philadelphia Museum of Art and The Barnes Fundations.
  2. Eat, eat, eat! Philly’s food scene is so underrated. We LOVE these restaurants: Heritage, Vista Peru, Harp & Crown, and Brauhaus Schmitz.
  3. Visit Philadelphia Distillery – A distillery, bar, and restaurant all in one. You can get all sorts of plates here, too. Everything I tried here was delicious and meticulously crafted.
  4. History – Philly is full of important American history. Check out the Liberty Bell, Independence Hall, and the Historic District.

How to Get to Philadelphia from NYC

  • Train: Take the Amtrak train. The cost varies on the times and train speed. The fastest gets you there in about 80 minutes!
  • Bus: From Greyhound to Megabus, there are so many cheap bus options to Philly.
  • Driving: I don’t recommend driving there unless you can pay for parking and are driving outside of the high traffic times. If you’re lucky, it takes 2 hours to drive into Philly from NYC.

17. Llama/Alpaca Hiking & Farm Experience

Hate the beach? That’s OK. How about an even more relaxing option? Hanging out with soft, cuddly llamas and alpacas. This is a great way to get to bring joy to your inner child, embrace your love for animals, and learn all about camelids (the biological family that llamas and alpacas are members of) from educator and homestead owner, Andrea.

Take a stroll with some of the llamas and alpacas through pastures and fields in either a private group or a large tour. You can even get a llama selfie in a perfect countryside setting.

18. Bear Mountain State Park

Located just over an hour’s drive north of Manhattan, this popular park has stunning views of the Hudson River, lush forests, and a variety of on-site activities. Hike the Appalachian Trail, enjoy a picnic by Hessian Lake, or take in the panoramic vistas from the Perkins Memorial Tower. Families can also enjoy the carousel and a seasonal outdoor pool.

19. Visit a Cider House in the Hudson Valley

Maybe you’re not feeling that active. How about spending your afternoon sipping on some ciders then? The Hudson Valley is apple country. And what can you make with apples? Cider. Delicious, crisp, tart cider. Apple cider used to be a common American beverage and cider houses in the Hudson Valley are bringing that mentality back. There are dozens of cider houses you can visit in the Hudson Valley.

Our Favorite Apple Cider Houses in the Hudson Valley

  1.  Twin Star Orchards – Twin Star Orchards often has live music, and you can buy food.
  2. Kettleborough Cider House – Kettleborough Cider House has one of the best views of Shawangunk Ridge.   

20. Westchester, New York

Westchester County is less than 30 minutes from Grand Central Station, and it offers several interesting places to visit. Unique activities include outdoor adventures, art museums, cute towns, and even breweries! You will not run out of things to do in Westchester on a day trip!

Highlight Things to Do in Westchester – NYC Day Trip

  1. Cranberry Lake Preserve: Explore local wildlife and plants as you hike through this 190-acre forest and quarry, which also boasts beautiful lakeviews and ponds. This hike is super easy and beautiful. Just avoid it during the buggy season.
  2. Anthony’s Nose: Don’t underestimate this 1.9-mile hike for its steepness, yet it will reward you with a breathtaking view of the Bear Mountain State Park. Moderately hard but safe and short distanced!
  3. Armour-Stiner Octagon House: This historic, octagonal Irvington home will take you back to the 19th Century. It also flaunts amazing art pieces and a recently restored greenhouse. Don’t miss the guided history tours.
  4. Sleepy Hollow Cemetery: More than a final resting place for several famous figures, this burying ground is a serene, stunning spot that offers guided and self-guided tours. 
  5. Celebrate Halloween: Westchester makes a great destination for a Halloween day trip if you want to step out of New York City in the fall. The annual Pumpkin Blaze in the fall illuminates thousand pumpkins for the enjoyment of children and adults alike. The enchanting Lyndhurst Mansion is also open for candlelight visits after dark.

How to Get to Westchester

  • Train: You can take the Metro North Hudson Line from NYC to Westchester in 30 minutes!
  • Bus: The bus ride from Madison Ave. to Westchester takes about an hour.
  • Car: Westchester is only 30 minutes driving from Manhattan. And minutes from the Bronx!

21. Guided Outdoor Day Trip Tours from NYC

There ya have it for some of the best day trips from New York City for every kind of traveler! If you have any questions or recommendations feel free to leave them below in the comments!

Pssstt… here’s a bonus New York recommendation for wine lovers: If you fancy a longer trip, consider heading further upstate to the Finger Lakes region. This area is perfect for wine lovers. Here, you can go on one of these amazing wine tours in the Finger Lakes which take you through some of the best wineries in the country.

Interested in more New York State travel ideas? Check out other popular NY travel guides:

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5 thoughts on “The Loveliest Day Trips From NYC for Food, Culture & the Outdoors

  1. Sebastian says:

    So the only thing you seem to care is about “Black lives matter” signs?
    Sheesh… I regret the google search that sent me to your website.

  2. Angela says:

    Thank you for this amazing list. I do plan on visiting some of them. I appreciate your listing the “Black Lives Matter” signs in two store windows, and your diverse photos of visitors. As an African American, it makes me feel more accepted and willing to venture out to new places. Great job!

  3. Marisol says:

    Great job on a comprehensive and detailed list! How could I know which of these are still doable in late Oct? I can imagine any water activity is out due to the cold??

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