The Most Beautiful Day Trip Destinations From New York City

Explore the outskirts of one of the most iconic cities.

For New Yorkers, Memorial Day Weekend presents the long-awaited opportunity to kick off summer with a scenic escape from the city. Whether you’re in the mood for a coastal beach getaway or an adventure in the woods, there’s a diverse range of landscapes within close proximity.

While a summer vacation usually entails a heavy amount of planning, weekend trips from NYC are easy to plan thanks to flexible transportation options. For example, one could hop aboard an Amtrak from Moynihan Train Hall and zip up to Hudson for a few days of vintage shopping and cafe hopping. In the mood for a dip in the ocean? Catch the Hampton Jitney from Manhattan and take it to one of Long Island’s famed beaches. And if you prefer your own set of wheels, even more options abound within just a couple of hours from the city.

Ahead, dive into the best trips from NYC for Memorial Day Weekend for every kind of traveler.

1. Small town charm in Beacon

The Hudson Valley is home to countless towns and villages with their own distinct charm. Beacon, about an hour-and-a-half from the city by train, is one such destination that’s ideal for a weekend getaway. Begin your trip with a visit to Dia Beacon, a world-renowned museum with works by Richard Serra, Andy Warhol, and Louise Bourgeois. (Also be sure to check out the current Steve McQueen exhibition.) You can spend the rest of your time meandering the main street, popping into cute cafes, artisanal craft shops, and local breweries for a craft beer.

2. Breathtaking trails in Cold Spring

Hop on the train at Grand Central for just over an hour and you’ll arrive at picturesque Cold Spring – a historic village with a network of breathtaking hikes and plenty of restaurants and shops to complement a day on the trails. Breakneck Ridge is the most popular trail (named after its steep scramble at the beginning), but you can also choose from other paths such as the Cornish Estate Trail, which leads to the fascinating ruins of a 1910 estate. After you’ve worked up a sweat, enjoy a cold beverage at Cold Spring Depot, then pick up some souvenirs from the local general store, Split Rock Books, and perhaps even the Cold Spring Cheese Shop.

3. Historic castles on Long Island’s Gold Coast

Resting majestically on the northern shore of Long Island, Huntington is a tranquil seaport town that was first settled back in the 1600s. Now, it’s home to beautiful estates, like the Oheka Castle. Believed to have inspired the real-life mansion from The Great Gatsby, the property’s owners hosted lavish parties throughout the heyday of the 1920s. Thankfully, it now operates as a hotel and estate, meaning guests can experience this opulent slice of history from suites inspired by the spirit of the Roaring Twenties on Long Island.

4. Canoe camping in the Adirondacks

If you’re in search of a rustic, nature-filled weekend getaway, grab your tent and sleeping bag and book a canoe up in the Adirondacks. This mountain range is a playground for outdoor enthusiasts with its vast wild landscape, but one particularly unique way to experience the region is by tossing all of your camping gear in a canoe and paddling out to sleep on an island (or two) for a few nights. With more than 3,000 lakes and ponds and 30,000 miles of rivers and streams, you’ll have plenty of locations to choose from (and a high likelihood of escaping the crowds).

5. Farm-to-table cuisine in the Hudson Valley

If your idea of the perfect getaway entails several pitstops for fantastic fresh cuisine, head for the Hudson Valley. This striking destination is not only beloved for its scenic views, but also its world-renowned farm-to-table cuisine. Make Hudson your home base for the weekend (Zio Cabin designed by Anthony D’Argenzio is a great pick) and zip around from iconic spots such as the Culinary Institute of America’s student-staffed restaurant, American Bounty as well as Blue Hill at Stone Barns. If you’re interested in artisan cheeses, make a stop at Sprout Creek Farm and don’t miss the fresh, rotating menu at WM. Farmer and Sons in Hudson.

6. Beach culture in Montauk

The Hamptons in the summer are a vibe. Towns and villages like Amagansett, Sagaponack, and Sag Harbor are all top-notch destinations, but there’s nowhere quite like Montauk. With its sprawling white sand beaches and distinct surf culture, it’s a place everyone should make a summer pilgrimage to at least once. Naturally, the crowds are denser on the weekend, but why let that stop you from joining the fun? Montauk is at the easternmost tip of Long Island (sometimes referred to as the ‘edge of the world’) and is reachable via the iconic Hampton Jitney bus. For a quieter side of Montauk, book a room at Marram, a 96-room oceanfront boutique hotel with impeccable design and noteworthy wellness programming.

7. Wine Tasting in Niagara Falls

The falls of Niagara are approximately 12,000 years old, formed by melting glaciers and flowing from 187 feet high. Naturally, a visit to this incredible spectacle is a must-do if you’re in the area, but a weekend trip here should also entail an itinerary of wine tasting. The area is renowned for its ice wine, but there’s much more to explore here than the iconic sweet wine. Need a few suggestions? Start at LEED-certified Stratus Vineyards for a pour of their delicious Cabernet Franc followed by a stop at Hidden Bench Estate Winery for a tasting in a barn-like setting. Also of note is Cave Spring Cellars for their brilliant Rieslings, ranging from bone dry to ultra-sweet.

8. Biking along Lake Champlain in Vermont

Lake Champlain is one of the largest freshwater lakes in the states, running about 120 miles in length and 12 miles across at its widest point. Lake Champlain Bikeways takes full advantage of this with its bike routes that wind along stunning backdrops. 35 loops and tours ranging from 10 to 60 miles in length comprise the network, offering stops at historic sites, wildlife refuges, and charming country farms. For a few route ideas, explore this brochure from Vermont State Parks.

9. Cultural flair in the Berkshires

The Berkshires is a pristine region in western Massachusetts renowned for its scenic beauty and cultural attractions. The area is composed of several charming villages, like Lenox and Great Barrington, and a weekend visit here consists of historic sites, well-curated museums, unique local shops, and boundless natural splendour. While here, don’t miss Edith Wharton’s The Mount (the author’s former home) as well as a wander through Mass MoCA 250,000 square feet of gallery space.

Explore the outskirts of one of the most iconic cities.

The Most Beautiful Day Trip Destinations From New York City

Explore the outskirts of one of the most iconic cities.

1. Small town charm in Beacon

2. Breathtaking trails in Cold Spring

3. Historic castles on Long Island’s Gold Coast

4. Canoe camping in the Adirondacks

5. Farm-to-table cuisine in the Hudson Valley

6. Beach culture in Montauk

7. Wine Tasting in Niagara Falls

8. Biking along Lake Champlain in Vermont

9. Cultural flair in the Berkshires

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