5 Amazing Road Trips from New York City

We’re sharing 5 amazing road trips from New York City - all under 5 hours away! You won’t want to miss these incredible destinations.

Living a stone's throw away from the heart of New York City, we have both easy-access to the best city in the world AND direct-flights to everywhere else you could possibly want to see. Sometimes, it’s easy to forget how much there is to enjoy within too-close-fly range.

While we prefer to adventure further for our “big” vacations, we love a long weekend away and sometimes a road trip is the perfect option! No worries about flight delays, no TSA, less packing stress. Just your crew, a great playlist and a straight-shot to the fun!

Whether you’re local to the area or planning a summer vacation and want to use New York City as a jumping off point, there’s so much to discover within easy (and beautiful) driving distance of the New York Tri-State Area.

It’s nearly impossible to narrow down the list to a Top 5, but we’re giving you our picks based on places we’ve visited and loved or are in the process of planning for ourselves.

Using Midtown Manhattan as the starting point. Times may vary depending on where in the New York Tri-state area you are starting from.

Washington D.C. (4 hours)

We are of the strong opinion that Washington DC doesn’t get enough love among travelers – especially those in the North East. We’ve used Washington D.C as a stopover point on longer roadtrips down the East Coast and always feel like we never have enough time. Whether you’re exploring with the family or escaping for a few days away without kids, the city has something special for everyone – from museums to gardens, affordable to the bougie, historic to artsy.

What we love most about Washington DC:

ABUNDANCE OF FREE ACTIVITIES

One of the most favorite aspects of Washington DC is how affordable it can be. Many of the city’s iconic landmarks, including the Smithsonian museums, the National Mall, and the memorials, are open to the public at no cost. If you think you’re not a museum person, think again. The Smithsonian museums are truly amazing and have something for everyone. Our Favorites? The National Air & Space Museum where you can see a Wright Brothers Plane, Neil Armstrong’s Spacesuit and (for the Disney Fans) the Buzz Lightyear that flew aboard the International Space Station. Also, the Museum of American History with a treasure-chest of Historic and Pop Culture Artifacts including Abe Lincoln’s hat, Julia Child’s kitchen, THE Star Spangled Banner which is truly special to see in person.

WALKABLE, BIKEABLE AND WELL CONNECTED

There’s no better way to soak up a destination than immersing yourself without ever needing to get into a car. We particularly love a city that can be discovered on foot! One of the most striking features of Washington DC is its walkability. The city’s easy-to-navigate layout, wide avenues, spacious sidewalks, and pedestrian-friendly paths, make it a joy to explore on foot.

Washington DC also boasts excellent public transportation options. Using the Metro network of subway and buses, visitors can effortlessly reach key landmarks, museums, and neighborhoods, without the hassle of D.C. traffic (which can get congested.)

DIVERSE HOTEL & ACCOMMODATION OPTIONS

Book a Mall-facing room at the JW Marriott on the 4th of July for a spectacular view of the National Fireworks.

From renowned hotel chains to charming boutique accommodations, Washington DC offers a wide range of options to fit every traveler’s style and budget. Whether you prefer luxury amenities, historic charm, or just need a clean and comfy place to fit the whole family, you’ll have plenty of options to choose from. We’ve personally stayed at the J.W. Marriott ($$$) and the Capitol Hill Hotel ($$) and loved both options; both within walking distance of the National Mall.

Bonus tip: For a truly special 4th of July, book a National Mall facing room at the JW Marriott for a front-row seat to the National Fireworks. We did this one year and it was worth the overnight! We ordered BBQ on grub-hub, “picnicked” on the beds, and watched the fireworks with the broadcast on in the background. If you’re a Disney fireworks lover, this experience is definitely for you.

GREAT FOOD!

Yellow, a Levantine cafe in Georgetown with Lebanese wines, pizzas, and dips. Visited in Netflix’s Somebody Feed Phil. Photo by Rey Lopez.

Whether you consider yourself a real foodie or just appreciate the chance to discover some unique spots you can’t find at home, Washington D.C. delivers! The city’s dining scene has experienced a renaissance in recent years, with a diverse range of amazing choices from Michelin-starred restaurants to cozy cafes and food trucks. (Sidenote: If you are travel and food lovers (like us) and considering D.C. it’s worth watching the Washington D.C. Somebody Feed Phil episode from the most recent season on Netflix.)

2. Cape May, New Jersey (3 hours)

We have a long list of “visit the place that inspired the Disney experience” destinations and Cape May ranks among the top we’re excited to visit. And, it’s an easy road trip from New York City and the surrounding area. As you may have already guessed from the namesake Disney dining hot-spot, Cape May served as the inspiration for one of our favorite Walt Disney World Resorts, the Beach Club. With its iconic Victorian architecture, sandy shores, and laid-back atmosphere, its not hard to imagine how Disney Imagineers were inspired to recreate the spirit of the destination.

Disney lovers can check off seeing the real-life version of Disney’s Beach Club.

What we can’t wait to explore in Cape May, New Jersey:

DREAMY SUN-KISSED BEACHES

Cape May boasts some of the most pristine beaches on the East Coast, offering the perfect spot for building sandcastles, splashing in waves, or simply soaking up the sun.

HISTORIC CHARM

We love destinations that make you feel like you stepped back in time or into a storybook. Cape May delivers big with well-preserved Victorian architecture, historic sites, and charming streets lined with quaint shops and eateries. Take the nostalgia to the next level with a horse-drawn carriage ride around town.

FAMILY FRIENDLY ACTIVITIES

From biking along scenic trails and exploring nature reserves to indulging in delicious ice cream and playing mini-golf, Cape May truly has something for everyone. For nature lovers like our family, National Geographic has listed Cape May as one of the world’s best birdwatching destinations in the world. Cape May is also a fantastic spot for year-round dolphin and whale watching. Hop aboard a 3-hour tour (a 3-hour tour) to see bottlenose dolphins, baleen whales and even humpback whales!

SEASIDE SWEETS & TREATS

No need for the namesake buffet here because the real-deal Cape May has it all with authentic beachside charm. Enjoy beachfront cafes, farm-to-table fare, fresh seafood and an endless number of ice cream spots. Just thinking about this trip we’re craving Salt Water taffy which originated just up the shore in Atlantic City. Fralingers looks like a must-visit. It’s so adorable and looks like it’s straight out of Charlie & the Chocolate Factory!

3. Lake Placid, New York

Lake Placid was an unexpected surprise for our family. Further than Lake George (home to the gorgeous Sagamore resort) but not as far and exciting as crossing the border into Canada, it was never really top of our list. But constrained vacation days around one of our milestone birthdays forced Lake Placid into consideration, with the country’s longest mountain coaster coaxing us to make the trip.

Deep into the pandemic and missing our regular trips to Walt Disney World, we were intrigued by the Whiteface Lodge which looked like a real-life version of the Wilderness Lodge. To say we were blown away by this trip is an understatement. The beauty of the Adirondacks, charm of Main Street, excitement of the outdoor activities and real-life rustic magic of the Whiteface Lodge stole our hearts. Best yet, Lake Placid truly is a year-round destination with great skiing in the winter, endless outdoor activities in the warmer months and some of the most stunning leaf-watching in the country come Fall, making it a truly amazing road trip from New York City and the surrounding areas!

Need more reasons to consider Lake Placid?

ADIRONDACK ADVENTURES FOR ALL AGES

While serious athletes will love the challenge of Lake Placid’s mountain biking, hiking or Olympic sites, you don’t have to be a seasoned outdoor enthusiast to enjoy the thrill of the Adirondacks.

Catch ski-jump competitions and practices year round and the Olympic Jumping Center.

Home to the 1932 and 1980 Winter Olympics, the former Lake Placid game sites offer visitors the chance to tour the grounds, experience some of the sports or watch current aspiring Olympians practice. The Cliffside coaster is a family-friendly must-do that lets you follow the path of the former luge track. Check out the Olympic Jumping Center schedule to watch ski-jump competitions or trainings. It’s incredible to see these athletes fly!

High Falls Gorge has paved hiking trails making it easy for all to enjoy.

When you’re ready to be immersed in nature, High Falls Gorge has a stunning waterfall that is easily accessible by a 30 minute, wheelchair accessible “hike” down a wide path. Whiteface Mountain is a MUST visit. Take a stunning drive to the near-top of the mountain where you’ll find an elevator INSIDE the mountain to take you to the summit. The cold, wet and dark tunnel carved through the center of the mountain was just as amazing as the view from the top!

RUSTIC OR LUXURIOUS ACCOMMODATIONS - OR BOTH!

Whiteface Lodge combines luxury with a family friendly atmosphere and authentic Adirondacks charm.

After a day of exploration, retreat to one of Lake Placid's inviting hotels, where families can unwind and indulge in creature comforts amidst stunning mountain vistas. Relax by the poolside, soothe tired muscles in a rejuvenating spa, and savor delectable dining experiences that cater to every palate.

We can’t say enough good things about the Whiteface Lodge. Swim in a heated pool, dine at one of the great restaurants, and make smores around the firepit. While the resort is not ON the lake, it has a beautiful private lakefront space with tables, concessions, bathrooms and a free shuttle.

For the Disney Lovers, Whiteface Lodge is the closest East Coast version of the real-life version of the Wilderness Lodge. This is such a great long-weekend destination for families who need a dose of magic and want to experience a real-life version of one of their favorite Walt Disney World resorts.

CHARMING MAIN STREET DELIGHTS

A trip to Lake Placid isn’t complete without a leisurely stroll down charming Main Street. Lined with boutique shops, art galleries, great restaurants, and treat-shops, you can easily shop and munch your way through a few hours on Main Street. Don’t miss the Adirondack Popcorn Company. There are so many great and unique flavors you’ll want to stock up. Grab a couple of bags to munch on for the road-trip home and then a comfort-treat for when you’re back on your couch, wishing you were back in the Adirondacks.

4. Newport, Rhode Island & Cape Cod, Massachusetts (3 - 4 hours)

We covered the inspiration-point for Disney’s Beach Club. Now we’re hitting the spots that give all the Yacht Club feels. It was a tough call on which of these 2 stops deserved a spot on our top-5 list. Lucky for all traveling from New York, you have to pass Newport to get to Cape Cod so we’re including both!

NEWPORT, RHODE ISLAND

If you’re looking for just a long weekend away, Newport stands up on its own with a perfect blend of history, charm, and coastal beauty. For families traveling to Newport, there's no shortage of activities to keep everyone entertained. Take a stroll along the Cliff Walk, offering breathtaking views of the ocean and the opulent mansions perched atop the cliffs. Or for a more hands-on experience, head to the Exploration Center and Aquarium at the Save The Bay Newport campus, where children can learn about local marine life through interactive exhibits and touch tanks.

The White Horse Tavern, Newport Rhode Island

Whether you’re staying for the weekend or stopping on your way to the Cape, no visit to Newport would be complete without indulging in Newports food scene. Sample freshly caught seafood at waterfront eateries like The Mooring Seafood Kitchen & Bar or indulge in a classic New England lobster roll at Anthony's Seafood. History-lovers (like us) will love The Black Pearl or The White Horse Tavern, the oldest operating tavern in the United States. This is also a great-spot for the Disney lovers who appreciate getting the real-world experience from some of their favorite park and resort spots. The White Horse Tavern will definitely give you Yacht Club or Liberty Tree Tavern vibes.

CAPE COD, MASSACHUSETTS

If you have time for a longer trip, continue past Rhode Island to Cape Cod to enjoy quaint New England villages, stretches of gorgeous dog-friendly beaches, bike paths and amazing fresh seafood. There are tons of home-rentals, small hotels and resorts to choose from.

The Chatham Bars Inn has been at the top of our dream vacation bucket list for years. It’s a true luxury resort with fantastic dining, amenities, a beach-front pool AND a fantastic kids club. The best of ALL worlds! The Disney lovers will get their full dose of real-life Yacht Club (but better) Resort here.

5. Kennebunkport, Maine (4 - 5 Hours)

I’m curious how many people got to number 5, saw Kennebunkport and thought “What? Not Boston!” Sorry, not sorry. Believe it or not, Kennebunkport is one of our favorite places we’ve ever been in the United States and is a frequent recommendation we make to friends, family and clients.

Stay right in the heart of Kennebunkport with a great selection of boutique hotels, inns and home rentals.

We thankfully discovered the magic of Maine and Kennebunkport in the summer of 2020 when the pandemic was still in full swing and we were looking for driving-distance destinations where we could be outside. We’ve been back since and often find ourselves daydreaming of the Goose Rocks Beach sunsets. There’s something about Kennebunkport that is indescribable and truly magical. The salt air, quintessential New England shops, beautiful shingle-side cottages, quaint ice cream and candy shops; it’s a kind of nostalgia and relaxation we’ve yet to experience elsewhere. We highly recommend adding Kennebunkport to your road trip list!

We’ll let you in on the magic of Kennebunkport.

GORGEOUS BEACHES & SPECTACULAR SUNSETS

No filter needed on the dreamy sunsets at Goose Rocks Beach.

Kennebunkport is renowned for its pristine beaches, where miles of soft sand meet the sparkling waters of the Atlantic Ocean. The shallow and very gradual shorelines make for amazing family-friendly swimming and low-tide exploration. During high-tide, you can swim out far and still only be about waist deep in gentle waves. When the tide retreats, walk a hundred+ feet out into the shallows to discover a world of cute little crabs and marine life underfoot.

As the day winds down, don't miss the chance to witness the truly spectacular sunsets. We loved ending our days with picnic blankets and snacks, watching the kids run around the sand with painted-pink, orange, and gold skies as a backdrop.

AMAZING OUTDOOR ADVENTURES

From biking to boats and everything in-between, Kennebunkport offers so many fun ways to enjoy the fresh sea air, relax and explore. The area offers a network of picturesque biking trails, including the Eastern Trail, which winds its way through lush forests and coastal marshlands. Pedal past historic lighthouses, charming seaside villages, and rolling farmland, immersing yourself in the natural beauty of Maine's countryside.

For a thrilling maritime adventure, embark on a whale watching or lobster boat excursion from Kennebunkport Harbor. Set sail aboard a comfortable vessel and cruise along the rugged coastline in search of humpback whales, dolphins, and even porpoises.

The Seashore Trolley Museum has over 300 vintage transport vehicles you can climb aboard, ride and explore.

For families with kids or train lovers (we have both), the Seashore Trolley Museum is a must. We spent a full morning here, riding and historic all the historic trolleys, busses, and trains. I don’t know who loved it more — the kids or the adults!

GREAT EATS & SEASIDE SWEETS

By this point you’ve figured out that great food ranks high on our list of must’s for an amazing vacation destination. From locally caught lobster and seafood chowder to farm-to-table fare and artisanal cheeses, Kennebunkport is a food-lovers dream. The Clam Shack, known for its legendary lobster rolls, is a Kennebunkport right-of-passage. We love having cocktails and a relaxing meal at the Boathouse restaurant on Main Street.

Mornings in Paris is a Magic Journeys team favorite and must-stop, with croissants, macarons and french pastries so delicious you’ll think you were sitting in France. Another favorite spot: Goose Rocks Dairy where we’ve had some of the best ice cream we’ve ever eaten in - our - life. We’d be lying if we said we haven’t contemplated a trip just to have this ice cream again.

Goose Rocks beach is the place we daydream about when we want to escape the stress of the real world.

As you set off on your road trip adventure from New York City, remember that the journey itself is just as important as the destination. Whether you choose to explore the coastal charm of Newport, the hidden gem of Kennebunkport, or any of the countless other scenic spots along the way, each destination offers its own unique blend of natural beauty, cultural richness, and unforgettable experiences. So, pack your bags, hit the road, and let the open highway lead you to new discoveries, cherished memories, and the joy of exploration. Happy travels!

5 Amazing Road Trips from New York City (Under 5 Hours Away!)