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  • Writer's pictureTaleen Krug

Weekend Getaways from Long Island, N.Y.


long island

The summer solstice occurs on June 21, marking the beginning of the vacation season and that means it's time to make summer getaway plans.


If you live or are vacationing in Long Island, while Long Island offers numerous attractions and activities, it may be worthwhile to explore other regions as well.


Buckle up and prepare for an unforgettable adventure through the breathtaking landscapes of closeby places ranging from the Hudson Valley to as far away as Philly.


Do get ready for an epic escapade (or several) that'll take you on a wild ride through the perfect blend of city and seaside.


Options Galore

Bask in the sunshine on Montauk and Southhampton's flawless beaches enjoy plenty of outdoor activities or hop aboard a ferry from Orient Point to tantalize your taste buds with the delectable cuisine of Long Island City, Queens, or Brooklyn. A weekend getaway is guaranteed to leave you breathless and revitalized.


Experience the magic of the summer with a thrilling mountain hike in the Catskills, where the vibrant flora and fauna will take your breath away. Or, set sail from Port Jefferson or Orient Point and discover the enchanting destinations of Boston and Cape Cod, where summer beauty meets seaside charm.

Don't miss out on wonderful weekend getaways and weekend trips from Long Island Embark on an extraordinary adventure where many enchantments and magic await your arrival.


With our suggestions, you can treat yourself to a delightful stay at a charming bed and breakfast for a romantic getaway or a cozy family resort and create unforgettable memories. Prepare yourself for unforgettable moments that will be forever etched in your mind!


Leave the chaos of Long Island behind and embark on an epic weekend adventure! Our exclusive selection of top destinations will take you on a journey to discover the most thrilling and unforgettable experiences that will leave you with memories that last a lifetime. Buckle up and get ready to explore!


1. Philadelphia, PA

If you're looking for a break from Long Island, consider Philly. It has a unique atmosphere and character, not just a copy of NYC. Philly has a history (Liberty Bell and Independence Hall), great architecture (LOVE sculpture and City Hall), and a delicious food scene (Reading Terminal Market, Federal Donuts, and more). There's also Old City, the Philadelphia Zoo, Logan Square, and Fish Town. Check out, Philly for tons of fun activities.

Embark on a 3-hour road trip covering approximately 140 miles/240 km of picturesque landscapes.


2. Sleepy Hollow, NY

sleepy hollow

How about a journey to the hauntingly captivating world of Sleepy Hollow legends? Take a trip to the historic landmark and town where Ichabod Crane vanished for an intriguing experience. Discover the history of Sleepy Hollow Cemetery and observe notable figures such as Elizabeth Arden, Andrew Carnegie, and William Rockefeller. And hold onto your hats, because that's just the beginning of the excitement. Brave the spine-tingling journey to the haunted grounds where the legendary headless horseman once galloped wild and free. Unveil the spine-chilling mysteries hidden within the walls of the Van Tassel homestead, Philipsburg Manor, the Old Dutch Church, and The Real Sleepy Hollow. Don't miss out on this hair-raising journey of a lifetime. Don't forget the interactive adventure through the Lyndhurst Mansion with "Sherlock Holmes: The Adventure of the Dying Detective" – a thrilling journey that explores the great detective's final case. Don't miss out on this immersive experience for thrill-seekers as you prepare for an epic escapade unlike any other!

The journey is approximately 64 miles/102 km, just a mere 1.5-hour drive away.


3. Hudson, NY

Hudson is a town that offers a blend of classic country and hip Brooklyn vibes. It has a variety of restaurants, bars, hotels, and fashion boutiques. The town is surrounded by historic rolling hills and beautiful scenery, making it an ideal spot for a relaxing getaway. Some recommended activities in the area include walking along Warren Street, browsing unique shops, touring the Olana State Historic Site, taking a boat tour of the Hudson-Athens Lighthouse, and trying the baked goods available for purchase from the Hudson Farmers Market. Hudson is a 3-hour road trip spanning 153 miles/246 km of adventure.


5. Catskills, NY

Get ready to explore the mountains! Spring and summer are the perfect seasons for hiking in Catskills - reach the summit and enjoy incredible panoramic views. With trails for all levels, beginners and thrill-seekers alike can find their ideal terrain. Want to try something new? Learn the art of fly fishing in its birthplace or brave the rapids with white water rafting. And don't forget to uncover the hidden gems of Catskills waterfalls.

Embark on a thrilling 3-hour road trip covering 153 miles/247 km of scenic beauty.


6. New Haven, CT

Discover the final resting places of famous politicians and war heroes at Grove Street Cemetery in New Haven. Take a page out of Rory Gilomore's book and explore Yale University, marveling at the Rare Book & Manuscript Library and Art Gallery. And let's not forget about the delicious local delicacies like Hamburger Sandwiches, Tomato Pie, and Fried Whole Bellied Clams. Ready for a weekend getaway? New Haven is calling your name, so start planning now!

Embark on a thrilling 2.5-hour drive spanning 107 miles/172 km!


7. Cape May, NJ

cape may

Escape Long Island and head to Cape May for the ultimate beach vacation. This hidden gem is New Jersey's "jewel in the crown" and boasts rich historical roots. Sink your toes into the soft sand and indulge in delicious seafood from one of many boardwalk or downtown restaurants. But the fun doesn't stop there! Take a tour of the Cold Spring Brewery, get spooked on a Ghost Tour, or catch a glimpse of dolphins in their natural habitat. Come experience all that Cape May has to offer!

This is a 4-hour road trip spanning approximately 209 miles or 344 km


8. New Paltz, NY

Escape to the stunning town of New Paltz for some much-needed R&R. Stay in the enchanting Mohunk Mountain House - a 150-year-old castle nestled in the Shawangunk mountains with breathtaking views of Lake Mohunk. Indulge in the luxurious spa, cozy up by the fire, or brave the great outdoors for thrilling winter activities such as ice skating, snowshoeing, or skiing. For a taste of city life, venture to Main Street where you can feast on farm-to-table cuisine, scour antique shops, snag rare finds at bookstores, sip on spirits at distilleries, and so much more.

About s120 miles or 193 kilometers, taking you on a thrilling 2.5-hour drive.


Head to Manchester, where summer is the season of enchantment! Feast your eyes on the dazzling foliage and check out this quintessential East Coast town with a plethora of delights, from fantastic breweries and locally sourced restaurants to mind-blowing art galleries, and picturesque natural scenery that will leave you spellbound. And before you leave, don't miss out on trying a divine Vermont cheese plate.

Get ready for a scenic journey spanning 237 miles/381km, or a 4.5-hour drive filled with endless possibilities.


10. Beacon, NY

Are you looking for a weekend getaway? Beacon, NY is a noteworthy location that is not as widely recognized. The destination provides a variety of attractions that encompass art, cuisine, wine, culture, and entertainment. Get ready for a weekend full of wonder at the Dia Art Foundation with its contemporary and minimalist installations, while Bannerman Castle, a Scottish gem in the middle of the Hudson River, will take your breath away. And for the adventure seekers out there, a climb up Mount Beacon will reward you with unbeatable views of the Hudson River Valley. Don't miss out on these must-see attractions. Experience the unique and unforgettable destination that you simply can't afford to miss.

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


Other Ideas

If none of the above floats your boast consider these other options from Long Island to explore this summer: Shelter Island, Lake Placid, Rhose Island, Lake Champlain, Atlantic City North Fork, Asbury Park Coney Sland, Lake George, Ellis Island, anywhere up and down the Gold Coast or Saranac Lake.

Discover A Perfect Escape Destination

Dreaming of a beach escape? Look no further than Cape Cod or Cape May! Wanting to discover a new city? Philadelphia and New Haven are calling your name. For a more rustic getaway, head to Beacon, Hudson, or New Paltz nestled in the mountainside. Once you've exhausted all the hiking trails and activities on Long Island, why not venture further out? With endless weekend destinations to choose from, we're sure you'll find the perfect getaway from Long Island, New York.


Wherever you decide to visit be it for a few weeks or days you're sure to have a grand old time in and around Long Island. From horseback riding to checking out the state's national park service, swimming in an outdoor pool, or just kicking back with some season-fresh produce on the beach, your getaway will be the best you've ever had!


If you're looking to relocate or visit Long Island or New York in general, be sure to hire professional Realtors like Taleene and Ritchie Krug Jr. who can find you exactly what you're looking for in terms of the best home, house, condo, or townhome. Lifelong residents of Long Island, are part of a team with more than 40 years of combined real estate experience. They have a deep understanding of how real estate has evolved through the years which results in a team with unique dynamics and expert negotiating skills being put to work on your behalf. With 20 offices spanning Brooklyn Queens & Long Island, nobody is better equipped to handle your real estate needs.

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