Weekend Trips from NYC: Small Towns and Getaways on Gossip Girl
From Blair Waldorf’s Yale ambitions to Serena van der Woodsen’s summers in the Hamptons, Gossip Girl regularly escaped Manhattan for grand estates, coastal villages, and historic college towns. Our Weekend Escapes from NYC series follows the characters beyond the Upper East Side—revealing the real small towns, filming locations, hotels, restaurants, and landmarks that brought the show’s most memorable getaways to life.
A Gossip Girl Weekend in the Hamptons
The characters spend the beginning of Season 2 in the Hamptons. Episode overview
Getting There from New York City
1. The Hamptons
By train: Take the Long Island Rail Road’s Montauk Branch from Penn Station or Grand Central Madison to Southampton, Bridgehampton, or East Hampton. Depending on the departure, you may need to transfer at Jamaica or Babylon. During the summer, the seasonal Cannonball provides express service from Manhattan. Check the MTA TrainTime app before leaving, as schedules change seasonally. View the LIRR Hamptons schedule
By car: From Manhattan, Allow approximately two to three-and-a-half hours, depending heavily on Hamptons traffic.
New Haven in a Day: Blair Waldorf’s Yale Weekend
The episode “New Haven Can Wait” sends the characters to Yale. Episode script
2. New Haven, Connecticut
if you’re a Gilmore Girls fan, you’re already familiar with this iconic fall foliage
By train: Take Metro-North’s New Haven Line from Grand Central Terminal directly to New Haven Union Station. Amtrak also operates from Moynihan Train Hall at Penn Station to New Haven, generally with fewer stops. Metro-North New Haven Line · New Haven Union Station
From Union Station, Yale and downtown New Haven are a short taxi, rideshare, bus ride, or approximately 20-minute walk away.
By car: I-95 North from New York City through Westchester County and coastal Connecticut to New Haven. The drive generally takes about two hours without significant traffic.
Some “Hamptons” scenes were actually created around Roslyn and Oyster Bay.
3. Roslyn and Oyster Bay
Long before it became the ideal setting for a Gossip Girl-inspired escape, Oyster Bay played a remarkable role in American history.
More than a century later, Oyster Bay became synonymous with Theodore Roosevelt. His family home, Sagamore Hill, served as the Summer White House from 1902 through 1908, bringing politicians, diplomats and international visitors to the village. Surrounded by historic estates, wooded roads and remnants of Long Island’s Gold Coast, Oyster Bay still feels connected to the world of old New York society. Settled in 1653, the waterfront community evolved from a colonial port and shipbuilding center into a hub of Revolutionary War espionage. Robert Townsend, one of George Washington’s most trusted Culper spies.
By train: Take the LIRR’s Oyster Bay Branch from Penn Station or Grand Central Madison. Get off at Roslyn for the historic village, or remain aboard until Oyster Bay, the final station. Some departures require a transfer at Jamaica or Mineola. View the Oyster Bay Branch schedule
By car: Queens–Midtown Tunnel to I-495 East. Visit Roslyn first, then continue north and east toward Oyster Bay using NY-106. Driving is the better option if you want to explore both towns on the same day.
Old Westbury and Long Island’s Gold Coast appeared in the series and perfectly captures its old-money aesthetic.more recently, you might recognize the property from some of your fave internet videos. It has remained an iconic backdrop.
4. Old Westbury Gardens
By train: Take the LIRR from Penn Station to Westbury Station, followed by a taxi or rideshare approximately 2.5 miles to the gardens.
By car: Take I-495 East to Exit 39 for Glen Cove Road. Follow the eastbound service road for approximately 1.1 miles, turn right onto Old Westbury Road, and continue for 0.4 miles. The public entrance is located at 71 Old Westbury Road. Official directions
Visitors should not use the private Post Road entrance.
Old Westbury Gardens filming history.
Upper Brookville: Inside the Mansion Behind famous White Party
The famous party property was actually on Long Island’s North Shore—not in the Hamptons. Mansion Global
5. Upper Brookville and the White Party Mansion
Upper Brookville is best reached by car. Take I-495 East toward Long Island’s North Shore, then continue north using Glen Cove Road/NY-107 or NY-106, depending on your destination.
Travelers without a car can take the LIRR’s Oyster Bay Branch to Greenvale, Glen Head, or Locust Valley and complete the journey by taxi or rideshare. The area is residential and is not practical to explore on foot.
The mansion associated with the Gossip Girl White Party is private property. It should be treated as television history—not as a public attraction or tour stop.
From Blair Waldorf’s Yale ambitions to Serena van der Woodsen’s summers in the Hamptons, Gossip Girl regularly escaped Manhattan for grand estates, coastal villages, and historic college towns. Our Weekend Escapes from NYC series follows the characters beyond the Upper East Side