Weekend Trips From the Upper East Side

Living on the Upper East Side means enjoying one of the most sophisticated neighborhoods in New York City. But even the most devoted city dwellers sometimes crave a break from the fast pace of Manhattan. Fortunately, there are several nearby destinations perfect for a weekend getaway. Whether you’re in the mood for a coastal retreat, a scenic drive through the mountains, or exploring a charming town, the East Coast offers plenty of options—all within a few hours of the Upper East Side.

So, where should you go on your next weekend escape?

For Upper East Side residents, the Hamptons are synonymous with summer escapes and luxurious beach living. Just a two- to three-hour drive from the city, depending on traffic, this string of villages on Long Island’s South Fork offers a mix of stunning beaches, high-end restaurants, and boutique shopping​.

Southampton and East Hampton remain the go-to destinations for many, thanks to their pristine beaches, art galleries, and upscale vibe. For a more laid-back experience, Montauk offers surf culture, casual dining, and beautiful hiking trails at Montauk Point State Park. Don’t forget to check out the famous Montauk Lighthouse while you’re there—it’s one of the oldest in the country.

But here’s the kicker: The Hamptons aren’t just for the summer. Many people are discovering the quieter charm of these villages in the fall and winter, with peaceful beach walks and cozy inns ready to welcome you year-round.

If you’re looking for a weekend filled with both nature and culture, the Hudson Valley is an excellent choice. North of the city, the region is home to charming small towns, beautiful hikes, and a growing number of farm-to-table restaurants​.

Beacon is a favorite destination for its blend of art and nature. The town is home to the Dia Beacon Museum, which showcases contemporary art in a vast industrial space along the Hudson River​. For those looking to get outdoors, head to Breakneck Ridge for a challenging hike with rewarding views of the river valley​.

On the other hand, if history is more your speed, don’t miss a visit to Hyde Park, home to the Franklin D. Roosevelt Presidential Library and Museum, along with the Vanderbilt Mansion​. It’s a great way to immerse yourself in New York history while enjoying the scenic beauty of the area.

For Upper East Siders craving a true retreat into nature, the Catskills offer an ideal weekend escape. Located about two hours north of Manhattan, this mountain region is known for its hiking, skiing, and relaxed vibe​.

Woodstock, the famous artsy town, draws visitors with its eclectic shops, art galleries, and live music. It’s a perfect destination if you’re looking to unwind and explore a creative community​. For those who want to get outdoors, there are plenty of hiking opportunities in the surrounding Catskill Mountains, including Kaaterskill Falls, one of the tallest waterfalls in New York State​.

The Catskills also shine in the winter, offering several ski resorts like Hunter Mountain and Windham Mountain, which are popular for weekend ski trips​. Cozy up by the fire in a rustic cabin after a day on the slopes, and you’ve got the perfect winter escape just a short drive from the city​.

If you don’t mind driving a bit further, the Berkshires in western Massachusetts are worth the trip. About three hours from the Upper East Side, the Berkshires are known for their scenic beauty and vibrant cultural scene.

The town of Lenox is a cultural hub, home to Tanglewood, the summer home of the Boston Symphony Orchestra. It’s the perfect spot for a weekend of world-class music, charming inns, and gourmet dining. Meanwhile, nearby Stockbridge offers the Norman Rockwell Museum, where you can explore the iconic works of the famed American painter​.

For outdoor lovers, the Berkshires provide numerous hiking opportunities in places like Mount Greylock, the highest point in Massachusetts, offering panoramic views of the surrounding countryside. In the fall, the region is famous for its stunning foliage, making it an excellent choice for a scenic weekend drive​.

Looking for a beach getaway with a completely different feel from the Hamptons? Fire Island, a narrow barrier island just off the coast of Long Island, is the perfect place to unwind in a car-free environment.

Accessible by ferry, Fire Island is a haven for those who want to escape the hustle of the city without sacrificing beautiful beaches and ocean views​.

Fire Island is made up of a series of small communities, each with its own unique vibe. Ocean Beach is the largest and offers a range of restaurants, bars, and shops, while quieter areas like Saltaire and Fair Harbor provide more low-key atmospheres​. It’s a great destination for a laid-back weekend of beach walks, ocean swims, and bonfires.

Here’s the interesting part: Since cars aren’t allowed on most of the island, you can rent bikes or simply walk around, making for a peaceful, traffic-free getaway​. Fire Island’s relaxed pace is perfect for those looking to fully unplug from the city.

For those willing to travel a bit farther, Newport, Rhode Island, offers a weekend filled with history, elegance, and breathtaking coastal views. A three-hour drive from the Upper East Side, Newport is famous for its Gilded Age mansions, many of which are open for tours​.

The Breakers, the Vanderbilt family’s summer home, is the most famous of these opulent estates, with its grand architecture and stunning oceanfront views​. After a day of exploring mansions, you can take a leisurely walk along the Cliff Walk, a scenic path that offers views of both the coastline and Newport’s historic homes​.

In addition to its history, Newport is also a great destination for sailing, seafood, and boutique shopping​. Whether you’re strolling the cobblestone streets or enjoying a lobster roll by the harbor, Newport is the perfect blend of New England charm and seaside luxury.

Living on the Upper East Side has many advantages, including proximity to some of the East Coast’s most desirable weekend destinations. If you're ready to explore real estate options that can give you access to these quick getaways, whether it's a pied-à-terre in the city or a second home outside Manhattan, reach out to The Kelly Robinson Team. Their expertise in Upper East Side luxury real estate will help you find the perfect home base for all your city and weekend adventures.