Top 13 Unforgettable Road Trips Near New York City

One of our favorite parts of travel is visiting local, boutique hotels and independently owned businesses. Whether you’re looking to escape the heat of an NYC summer or explore a nearby destination you’ve never seen before, these 13 road trips make for the perfect mini-break.

Here are the best road trips from New York City, from the most luxurious corners of New England to charming, up-and-coming Catskills enclaves.

1. Westerly, Rhode Island

A quaint coastal town overlooking the Atlantic Ocean, Westerly is a two-and-a-half-hour Amtrak ride or a three-hour drive from NYC. Visitors can explore the luxurious Ocean House, a Relais & Châteaux property that offers a private white-sand beach, the Mercedes-Benz Program, Ocean & Harvest Spa, and complimentary cooking classes at the Center for Wine & Culinary Arts.

2. Cape May, New Jersey

Cape May is one of the most picturesque towns on the Jersey Shore, showcasing attractions from the historic Congress Hall Hotel — opened in 1816 — to the paved promenade along its beaches. Visitors can enjoy fresh seafood at The Lobster House, followed by a sunset cocktail by the fire pits at the popular waterfront spot, Rusty Nail.

3. Finger Lakes, New York

Less than a five-hour drive from NYC, the Finger Lakes region is composed of 11 pristine lakes, award-winning wineries, and excellent hiking trails. For a luxurious escape, consider staying on Cayuga Lake at The Inns of Aurora. Guests can stay in the lavishly decorated Zabriskie House and participate in a cooking demonstration at Aurora Cooks, followed by a delightful cocktail at the hotel’s 1833 Kitchen & Bar. Visitors can also taste exquisite pinot noirs at Heart & Hands Wine Company or enjoy a peaceful day hiking at Watkins Glen State Park.

4. Alexandria, Virginia

Venture to Old Town Alexandria for a unique experience away from the bustling streets of NYC. Architecture enthusiasts will appreciate Old Town’s 18th- and 19th-century facades, while those looking to indulge in shopping will enjoy the vibrant local businesses. Alexandria, located right on the Potomac River, is one of the most charming southern cities, being just four hours away from NYC by car.

5. Catskills, New York

Cooperstown is reachable in a four-hour drive from NYC, navigating through the beautiful Catskill Mountains. Visitors can stay close to Otsego Lake at The Inn at Cooperstown, an award-winning hotel with 18 elegant guest rooms. From here, a short ride takes you to the north end of the lake and Glimmerglass State Park, a delightful spot for outdoor exploration.

Alternatively, the charming town of Roxbury in the Catskills is a quick three-hour drive from NYC. Stay at The Roxbury at Stratton Falls, a unique boutique hotel marked by its eclectic decor. Stargazers will delight in booking the astronomy-focused Galileo’s Gate cottage, complete with its own glass-ceiling observation deck.

6. Pocono Mountains, Pennsylvania

The Pocono Mountains serve as an easy getaway from New York City, with a travel time of just under two hours. For those seeking full nature immersion, consider a stay at Cranberry Run Campground. Surrounded by 65 acres of woodlands, visitors can relax at the outdoor pool or explore the nearby Delaware Water Gap National Recreation Area, featuring opportunities for hiking, canoeing, kayaking, and rafting.

7. Lexington, Massachusetts

Located approximately 15 miles from Boston, Lexington is the ideal destination for history enthusiasts. Stay at the stunning 22-room Inn at Hastings Park, a Relais & Châteaux property conveniently situated near Walden Pond, Battle Green (the site where the first shots of the Revolutionary War were fired), the Hancock-Clarke House, and the Orchard House (which inspired “Little Women”). This picturesque town can be reached in less than four hours from NYC.

8. Niagara Falls, New York

Traveling approximately 400 miles north of NYC takes you to the majestic Niagara Falls. The journey features scenic landscapes, with ample opportunities for hiking and picnic lunches along the way. Upon reaching Niagara Falls State Park, visitors are greeted by the stunning rainbows, mist, and the thunderous roar produced by the American, Horseshoe, and Bridal Veil Falls.

9. Newport, Rhode Island

Only a four-hour drive from NYC, Newport is a must-visit for all East Coast road trippers. This summer, indulge in luxury at The Vanderbilt, boasting 33 rooms in a historically significant mansion. The property underwent a recent renovation, offering unique experiences such as a wine tasting complemented by a vinyl listening session and tea leaf reading sessions with a professional psychic.

10. Haines Falls, New York

The Catskills deserve acclaim not just for one, but for several reasons. With majestic waterfalls, charming towns, and breathtaking scenery, this region is a treasure for outdoor enthusiasts. Haines Falls, located within the Great Northern Catskills, is home to Kaaterskill Falls—New York’s highest cascading waterfall. The trail is open year-round and features a round-trip length of about a mile and a half. Additionally, road trippers should explore Round Top to view Glen Falls, a popular swimming hole during the warmer months.

11. The Berkshires, Massachusetts

Embarking on a three-hour drive from NYC lands you in the stunning Berkshires of western Massachusetts. While visiting, indulge in iced coffees and croissants from Six Depot Roastery & Cafe and enjoy a picnic along Shaker Mill Pond. For a quintessentially charming New England experience, consider staying at The Old Inn on the Green.

12. North Fork, New York

Take a trip to the North Fork of Long Island, known for its fantastic dining and wineries, while still offering a quieter atmosphere than the hustle and bustle of the South Fork. While heading to the North Fork from NYC, consider stopping for lunch at Jerry & the Mermaid. Your first winery should be Bedell Cellars. On the return trip, if in season, be sure to visit the lavender fields at Lavender by the Bay.

13. Keene Valley, Adirondacks, New York

The Adirondacks are a year-round destination worth exploring. Keene offers access to some of the highest peaks, presenting incredible downhill and cross-country skiing during winter and excellent hiking during the summer, with trails like the Giant Mountain trail at Roaring Brook Falls being particularly recommended. For a lovely bed-and-breakfast experience, consider staying at the Keene Valley Lodge.