Quick Getaways from New York City: Long Weekend Road Trips

New York City is one of the world’s most iconic cities, as a hub for fashion, finance, and art it is often the best place to be if you want to be in the middle of the action. However, we all need a switch in scenery from time to time and New York City is not the only place available to have an iconic experience.

Let's look at the best places to visit near New York City!

1. Pocono Mountains, PA: 2 Hours

Distance from New York City: Approximately 2 hours

When you think of city living, you would think of New York City: tall buildings, train stations, a city that never sleeps. Every now and then you may need a break from the constant hustle and bustle.

Luckily, just two hours away is Pocono Mountains, PA. This mountainous region is the perfect place to unwind, reconnect with nature, and have an adventure that New York City can’t offer.

Pocono Mountains have everything you could wish for all in one place! Whether you want to go white water rafting, ATV riding, skiing, or just take a relaxing walk on a nature trail, Pocono Mountains have it all. You could also visit a winery, casino or a music venue for a nice night on the town.

Options for exploration in the Pocono Mountains include:

• Hiking, waterfalls, and exploring nature: Visit Bushkill Falls (the “Niagara of Pennsylvania”), explore trails at Hickory Run State Park, or hike to the scenic overlooks at Big Pocono State Park.
• Getting your fill of casinos, shopping, and indoor fun: Try your luck at Mount Airy Casino, shop at The Crossings Premium Outlets, or explore indoor water parks like Kalahari or Great Wolf Lodge.
• Relish in spa days and romantic atmosphere: Book a cozy retreat with in-room jacuzzis or treat yourself to a relaxing massage.

If you are looking to relax and unwind, you can visit the spa and get a massage, or try out some yoga. The possibilities are endless, and to explore them all you are going to need the perfect place to stay. Pocono Mountain Rentals offer impeccable quality and a luxury experience unlike anything else.

These gorgeous mountain homes are one-of-a-kind with amenities such as fire pits, hot tubs, scenic views, and so much more!

2. Ocean City, MD: 4 Hours

Distance from New York City: Approximately 4 hours

Although New York City has a beach, it is far from providing the beach town feeling that we all love so much. Fortunately, a short four hour drive away is Ocean City, MD, the perfect place to experience a true beach town, from the boardwalk to the ferris wheel.

This coastal city is bursting at the seams with adventure and excitement, offering countless options for delectable cuisine, dinner cruises, horse-back riding, tours, exciting attractions, and lively bars. In Ocean City, there is truly something for everyone!

Options for exploration in Ocean City include:

• Adventuring the area with water sports and boat rides: Try jet skiing, parasailing, paddleboarding, or hop on a dolphin-watching cruise.
• Hitting the beach and boardwalk: Spend the day lounging by the waves or explore the lively 3-mile boardwalk filled with arcades, shops, and classic eats like Thrasher’s Fries and Fisher’s Popcorn.
• Riding the rides: Trimper Rides and Jolly Roger Amusement Park offer nostalgic fun for all ages, from roller coasters to mini golf.

For the best beach town vacation, you also need the best beach house. Seaside Vacations & Sales offers luxury condos and townhouses that exemplify the bright, airy, feel of the coast with an air of extravagance and comfort.

With these homes being within walking distance to many of Ocean City’s most popular attractions, there is truly no better place to be!

3. Chincoteague Island, VA: 5 Hours

Distance from New York City: Approximately 5 hours

This charming little town is the perfect mix between a nature retreat and a beachside adventure, located just five hours from New York City, it is truly the best of both worlds! Notable for their incredible pony swims, Chincoteague is the place to renew your connection with both the land and the water in the cutest way possible!

If horses are not your thing then no worries, there is a lot more to do on Chincoteague Island. Enjoy activities such as fishing, surfing, biking, kayaking or relaxing on the beach, there is truly something to suit everyone’s tastes.

Options for exploration in Chincoteague include:

• Getting familiar with wildlife: Visit the Chincoteague National Wildlife Refuge and catch a glimpse of the famous wild ponies, or soak up the sun at Assateague Island’s serene beaches.
• Tasting fresh seafood: Enjoy dining at restaurants like Bill’s Prime Seafood & Steaks, Ropewalk, or Captain Zack's Seafood, where crab cakes and oysters are a must.
• Kayaking and paddleboarding: Paddle through the water, where you might spot dolphins, herons, and more.
• Exploring the downtown area: Browse local boutiques, bookstores, and artisan shops like Sandpiper Boutique, Sundial Books and Flying Fish Gallery.

As always, we know the perfect vacation is nothing without the perfect place to stay. Seaside Vacations & Sales has you covered in Ocean City and Chincoteague Island. These chic coastal homes include private balconies and stunning views, the cherry on top for a perfect vacation. An experience of true luxury and quality can always be found with Seaside Vacations & Sales.

4. Washington D.C.: 5 Hours

Distance from New York City: Approximately 5 hours

As capital of the United States, there is no shortage of things to see, do, and learn in Washington DC. Located just five hours from New York City, this historic city is a hub for politics, history, culture, and so much more. Home to iconic locations such as the Smithsonian Museums, The National Mall, The White House and so much more.

Being that this city is an endless well of excitement and wonder, you may need to make a few trips in order to experience all that it has to offer! Regardless of if you decide to do as many things as you can over one weekend, or split them up over the course of many, we have the perfect place for you to stay for every visit.

Options for exploration in Washington D.C. include:

• Discover iconic monuments and museums: Explore the National Mall, the Lincoln and Jefferson Memorials, and the world-class Smithsonian National Museum—all free to the public.
• Embrace art, culture, and live music: Catch performances at The Kennedy Center, browse galleries at the Hirshhorn Museum, or take in murals and music in The Wharf or 14th Street.
• Walking historic neighborhoods: Stroll through Georgetown’s cobblestone streets, Eastern Market in Capitol Hill, or U Street Corridor.

Home Sweet City offers luxury rental homes where every desire is catered to. Located in some of DC’s most coveted neighborhoods, these homes offer space, privacy, and luxury in the perfect location for you to get the most out of every stay.

With private parking and a rooftop terrace, this level of extravagance and convenience is something you will require and desire when visiting DC.

5. Finger Lakes, NY: 5 Hours

Distance from New York City: Approximately 5 hours

If you prefer to stay in-state, then this may be the perfect long weekend destination for you. Located just five hours from New York City, Finger Lakes is a gorgeous destination known for its outdoor activities, rich culture, and scenic views. The perfect place in the state of New York to get away from the hustle and bustle of New York City.
Finger Lakes is home to a group of eleven narrow and long glacial lakes, hence the name. Along these lakes you can enjoy the beauty of nature unlike ever before through waterfalls, gorges, a number of water activities, and scenic hiking trails. If you are looking for more than just a look at nature, Finger Lakes is also renowned for its incredible vineyards and a growing number of breweries. This charming destination is the switch up from New York City that you need!

Options for exploration in Finger Lakes include:

• Dining at local restaurants and farmers markets: Dine at tasty eateries like FLX Table, Moosewood Restaurant, and Kindred Fare, and browse fresh produce and crafts at local markets throughout the region like The Windmill Farm & Craft Market.
• Visiting wineries: There are plenty of wineries in the region, and you won't want to miss favorites like Dr. Konstantin Frank Winery, Hermann J. Wiemer Winery, and Ravines Wine Cellars.
• Exploring waterfalls and hiking trails: Discover stunning natural beauty at Watkins Glen State Park, Taughannock Falls, and Buttermilk Falls.

While enjoying the beauty of Finger Lakes, Linger Hospitality will provide the beauty in your home. These rental homes are the picture of perfection whether you want a hillside cabin just steps from a gorgeous waterfall, or a luxurious lakeside home with it's own private beach, Linger Hospitality can provide!

6. Killington, VT: 5 Hours

Distance from New York City: Approximately 5 hours

For all outdoor enthusiasts and nature lovers, Killington, VT is the perfect destination for your next long weekend vacation! Located just five hours from New York City, this city is the perfect place for all things outdoor adventure!

If you enjoy mountain biking, skiing, hiking, or even just a little golf, Killington has you covered!

Options for exploration in Killington include:

• Hiking, mountain biking, and scenic views: Tackle trails like the Thundering Falls Boardwalk, Killington Peak via Bucklin Trail, or explore the expansive Green Mountain trails.
• Dining at slopeside spots: Enjoy eateries like The Foundry at Summit Pond, Casey’s Caboose, Liquid Art Coffeehouse, and Sushi Yoshi.
• Exploring the local brew-scene: Grab a pint at Long Tail Brewing Company or the Killington Distillery! Or, you can enjoy live music and mountain views at the Lookout Tavern.

Also home to a growing craft beer scene, you can find tasty farm-to-table options at many restaurants. Many events and festivals are also hosted year-round in Killington, meaning there is always something new and exciting to do regardless of when you visit!

For the perfect place to stay when visiting Killington, GetAway Vacations is the only option! Offering the most exceptional vacation rentals in Killington, GetAway Vacations offers luxury and convenience regardless of what you are looking for in a home, whether it be a condo, cabin, or villa, they have you covered!

7. Stowe, VT: 6 Hours

Distance from New York City: Approximately 6 hours

Stowe, VT is a charismatic town where New England charm and outdoor adventure meet is the most perfect of ways. Located six hours from New York City, this is a trip you will not regret and never forget!

As one of the top ski destinations in the Northeast, Stowe offers skiing, snowboarding, and so much more at all levels on Mount Mansfield, the highest peak in Vermont. If you are not interested in winter sports, then you can always enjoy a number of hiking trails, mountain biking, zip-lining, a trip to the spa or wandering around the village of Stowe. Regardless of your interests, there is something appealing for you to explore and experience in Stowe.

Options for exploration in Stowe include:

• Hiking, biking, and scenic views: Explore the Stowe Recreation Path, Stowe Pinnacle Trail or Sterling Pond Trail.
• Dining at cafés and top-rated eateries: Get the best flavors from Plate, Harrison's Restaurant, or the iconic Hen of the Wood nearby for farm-to-table flavor. For breakfast, don’t skip Butler’s Pantry or Black Cap Coffee & Bakery.
• Soaking up relaxation and wellness: Book a spa day at Topnotch Resort or The Spa at Spruce Peak, or unwind in nature with a peaceful forest walk or yoga in the mountains.

When you are ready to wind down for the night, you can find relaxation, comfort, and luxury with Stowe Resort Homes. These open-concept mountain homes combine quality and convenience with gorgeous fireplaces, private hot tubs and resort amenities such as a ski valet and a nearby pond for ice skating and fishing!

You truly can never go wrong but will always find yourself just right when staying with Stowe Resort Homes.

8. Harpers Ferry, WV: 5 Hours

Distance from New York City: Approximately 4.5-5 hours

Harpers Ferry fuses American history and outdoor recreation into one accessible package. This West Virginia town, positioned where the Potomac and Shenandoah rivers meet, offers a refreshing break from city life.

The surrounding area presents the perfect scenery, with access to kayaking, rock climbing, and hiking - and access to the Appalachian Trail! With Civil War history, outdoor adventures, and a break from reality - Harpers Ferry truly delivers a trip to remember.

Options for exploration in Harpers Ferry include:

• Exploring rich history and landmarks: Tour the Harpers Ferry National Historical Park, visit John Brown’s Fort, and walk the preserved 19th-century streets where Civil War and abolitionist history comes to life.
• Visiting nearby wineries and breweries: Sip local flavors at places like Breaux Vineyards, Hillsborough Winery & Brewery, or Harpers Ferry Brewing with views over the river valley.
• Strolling through local shops and galleries: The Historic Lower Town houses museums and local shops. Wander through charming storefronts like Tenfold Fair Trade Collection, The Vintage Lady, and True Treats Historic Candy.

Mountain Mama, our 100 Collection partner, started with owners, Eddie and Mary’s, love for the area. Their properties have everything required to help you melt away in relaxation on this beautiful mountain getaway. These homes put you minutes from both hiking trails and historic sites, making it the perfect “un-plug” getaway.

9. Martha’s Vineyard: 5 Hours

Distance from New York City: Approximately 5 hours

If you thought New York City had good food, shopping, and exploration, Martha's Vineyard will captivate you. Those who appreciate New York's hustle find a perfect counterbalance in the Vineyard's slower-paced, charming lifestyle that still maintains rich cultural depth. In true Northeast fashion, you'll discover restaurants serving exceptional pizza pies, fresh lobster rolls, and just-caught clams.

Options for exploration in Martha's Vineyard include:

• Beach hopping and scenic views: Visit the majestic Aquinnah Cliffs, peaceful morning bike rides through natural settings, and relaxing beach days await in Martha's Vineyard! Other popular spots include Polly Hill Arboretum, Cedar Tree Sanctuary, and Edgartown Lighthouse.
• Discovering charming boutiques galore: Explore treasured finds like Slip 77, The Green Room, and Suka Boutique!
• Exploring nearby restaurants: Savor seafood at hotspots like The Port Hunter, Larsen’s Fish Market, and 19 Raw Oyster Bar. Don’t miss Back Door Donuts for an iconic island treat.

Trade your New York City apartment for a spacious, thoughtfully designed Martha's Vineyard vacation rental. Point B Realty homes provide the perfect environment to relax and rejuvenate, offering a quiet retreat from city life. From saltwater pools and bluestone patios to media rooms with premium sound systems, these properties have everything needed for a complete escape.

Each home showcases magazine-worthy features—interior elements like exposed beams and cozy fireplaces complement outdoor spaces with welcoming porches and meticulously maintained grounds.

The next time you find yourself itching for new scenery, different from what New York City has to offer, visit one of these incredible destinations for an unforgettable experience. New York City is an icon all on its own, but there are wonders to be discovered on the other side of its doorstep.