10 Best Weekend Trips From Long Island, New York - Updated 2021

weekend getaways from long island
Kavita
Kavita
Updated

Long Island is a beautiful place with so much to see and so much to do. It’s an island with city life, beach life, and everything in between. You can relax on the beaches of Montauk or Southhampton, catch a ferry from Orient Point, or travel west for some of the best cuisines you’ll taste in Long Island City, Queens, and Brooklyn! But what happens when you’ve lived here all your life or just want something new to do? Well, you’re in luck because Long Island is also conveniently located so you can take some of the best weekend getaways! Want to go hiking and see some fall foliage from the top of a mountain? Head to the Catskills! More into sailing? Then catch the ferry from Port Jefferson or Orient Point to Boston or Cape Cod! Whatever your desire, it’s definitely just a short trip away. If you have a long weekend coming up, visit Long Island, book a stay at a family resort or a cozy bed and breakfast, and plan your next adventure. Keep reading for a list of the best weekend trips from Long Island, New York.

1. Philadelphia, PA (from USD 36.0)

Philly skyline
Source: Photo by user https://www.flick... used under PUBLIC DOMAIN

If you’re tired of hanging out in NYC or just want to check out another major east coast city then Philly should be at the top of your list. While many may compare Philly to NY, it also has its own unique culture as well. It’s a beautiful and cosmopolitan city with deep historic roots (check out the Liberty Bell and Independence Hall), has an amazing architecture with historical nuances (LOVE sculpture and City Hall), and an amazing collection of restaurants, bars, and nightlife (some of my favorites include everything at Reading Terminal Market, Federal Donuts, Spruce Street Harbor Park, Independence Beer Garden, and Mission Taqueria). Other places you want to check out on your visit are Old City, the Philadelphia Zoo, Logan Square, and Fish Town.

Approximately 140 miles/240 km (3-hour drive)

Philadelphia City Sightseeing Hop-On Hop-Off Bus Tour

Duration: 30 to 60 minutes

10 reviews

2. Sleepy Hollow, NY

Sleepy Hollow Lake Drone image
Source: Photo by user Jameschuston used under CC BY-SA 4.0

Growing up you probably heard about the Legend of Sleep Hollow and now is your chance to actually see the town where Ichabod Crane mysteriously disappeared from. On your visit to this spooky town, you can take a tour of the Sleepy Hollow Cemetery to see Elizabeth Arden, Andrew Carnegie, and even William Rockefeller. You can also continue your visit with a tour of all the haunted sites the headless horseman frequented, like the Van Tassel homestead, Philipsburg Manor, the Old Dutch Church, and of course The Real Sleepy Hollow. If you’re looking for even more to do, then definitely check out “Sherlock Holmes: The Adventure of the Dying Detective” an interactive journey through the Lyndhurst Mansion and Sherlock Holmes’ last case.

Approximately 64 miles/102 km (1.5-hour drive)

3. Hudson, NY

Warren Street west view, Hudson, NY
Source: Photo by user Daniel Case used under CC BY-SA 3.0

Hudson is a hidden gem and the perfect spot for a relaxing getaway. This charming town is a conglomeration of the classic country town and Brooklyn. It has a wonderful array of restaurants and bars, trendy hotels, and fashion-forward boutiques, but all in within the backdrop of a historic town with rolling hills and stunning, serene scenery. While you’re visiting, I would definitely recommend strolling along Warren Street, maybe pop into some of the quirky shops along the way, check out Olana State Historic Site, take a boat tour of the Hudson-Athens Lighthouse, and even grab some fresh baked goods and maybe a meal at the Hudson Farmers Market.

Approximately 153 miles/246 km (3-hour drive)

4. Cape Cod, MA (from USD 55.0)

Cape Cod

If you’re planning your getaway in the warmer months, you might find the beaches a little crowded you’ll still enjoy their beauty and find some spots all to yourself. The cooler months might be a little too cold for a dip in the ocean but you won’t be able to stop admiring the breathtaking views of the Cape. While you’re here, you’re going to want to explore the Cape Cod National Seashore, Provincetown, Martha’s Vineyard, and maybe even take a quick trip to Nantucket! And don’t forget to try some of the iconic foods of Cape Cod including Lobster Rolls, an Apple Bear Claw (try Pie and the Sky) and of course, some homemade ice cream from Somerset Creamery.

Approximately 204 miles/328 km (3.5-hour drive)

All Island Bus Tour

Duration: 3 hours

2 reviews

5. Catskill, NY

Catskills
Source: Photo by user minka6 used under CC BY 2.0

Time to take a visit to the mountains! In the spring and fall, you can hike the mountain. Make it to the top and you’ll be rewarded with panoramic views. There are mountains for all hiking levels - flat trails for beginners and more vertical terrains for the adventure seekers. If you’re headed over there in the winter, then you’ll definitely have to visit one of the top ski mountains - Hunter or Windham! You can also learn to fly fish in the origin of fly fishing, go white water rafting, or search for the secret Catskills waterfalls.

Approximately 153 miles/247 km (3-hour drive)

6. New Haven, CT (from USD 12.0)

Phelps Hall and Lyceum, Yale College, New Haven, Connecticut, 1901
Source: Photo by user Detroit Publishin... used under PUBLIC DOMAIN

While in New Haven, you can explore the Grove Street Cemetery to see the final resting places of famous politicians, war heroes, signers of the Declaration of Independence, and more. Then, channel your inner Rory Gilmore, wander through Yale University, and check out sites like the Rare Book & Manuscript Library, Art Gallery, and more. And while you’re in New Haven, don’t forget to enjoy some of the local delicacies like the Hamburger Sandwich, Tomato Pie, and Fried Whole Bellied Clams. You will love a weekend getaway in New Haven, so you better start planning.

Approximately 107 miles/172 km (2.5-hour drive)

New Haven Scavenger Hunt: Yale & Beyond

Duration: 2 hours

7. Cape May, NJ (from USD 45.0)

Cape May Beach Ave from the sea 3
Source: Photo by user Smallbones used under CC0

Cape May is the perfect place to go for a beach vacation away from Long Island. This destination has deep historic roots and is considered New Jersey’s “jewel in the crown”. While you’re here, you can relax on the sandy beaches, grab a bite to eat at one of the restaurants on the boardwalk or in town - you can get some of the best seafood here! And then don’t forget to check out other unique sites like the Cold Spring Brewery, take a Ghost Tour, or go dolphin watching!

Approximately 209 miles/344 km (4-hour drive)

Whale and Dolphin Watching Cruise from Cape May

Duration: 3 hours

5 reviews

8. New Paltz, NY

Downtown New Paltz, NY
Source: Photo by user Daniel Case used under CC BY-SA 3.0

New Paltz is a beautiful town that’s perfect for some R&R. You can stay at the amazing Mohonk Mountain House - actually a 150-year-old castle in the Shawangunk mountains at the edge of the picturesque Lake Mohonk. At the resort, you can relax in the spa, snuggle up in front of the fireplace, or adventure outside for some winter activities like ice skating, snowshoeing, skiing, etc. If you want more of a downtown experience, you can venture to Main St and enjoy all that New Paltz has to offer like farm to table restaurants, antique shops, book stores with rare finds, distilleries, and more.

Approx 120 miles/193 km (2.5-hour drive)

9. Manchester, VT

Main Street, Manchester Center, VT
Source: Photo by user John Phelan used under CC BY-SA 4.0

While Manchester is a beautiful town to visit at any time of the year, it is especially beautiful in Autumn, when you can fully appreciate the foliage while drinking you PSL. Manchester is a quintessential East Coast town, so while you are here, you can check out fantastic breweries, locally sourced restaurants, amazing art galleries, and of course, the picturesque natural scenery all around you. And don’t forget to try a Vermont cheese plate before you leave.

Approximately 237 miles/381km (4.5-hour drive)

10. Beacon, NY (from USD 61.0)

Beacon NY 5
Source: Photo by user AlexiusHoratius used under CC BY-SA 4.0

Last but not least is Beacon, NY, a town you should most definitely consider for your weekend getaway. Beacon is a beacon for anyone who enjoys art, food, wine, culture, and fun. You can start your weekend at Dia Art Foundation, which has dozens of installations ranging from visual art to contemporary to minimalism and the list goes on. Then head to Bannerman Castle, a Scottish castle in the middle of the Hudson River. And if you want the best view of the Hudson River Valley, then you have to climb Mount Beacon. The views are incomparable.

Approx 98 miles/158 km (2-hour drive)

Food Tour of Beacon in the Hudson Valley

Duration: 3 to 30 minutes

Find your next getaway destination

Were you hoping for a beach getaway, because then Cape Cod or Cape May would be perfect! Or maybe you want to explore a new city like Philadelphia or New Haven? Or you can even just go to a rustic mountainside town like Beacon, Hudson, or New Paltz. After exploring all the hiking trails and things to do in Long Island, venture further out. There are so many great places to go for a weekend, so we hope you’ve found the right one for you!

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Kavita is an avid traveler, enthusiastic foodie, and aspiring Instagrammer, whose life goal is to renew her passport because she’s maxed out her stamp pages. Kavita’s wanderlust started from a...Read more

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