53 Hill St, Southampton, NY 11968
(631) 600-7700
As summer draws to a close, now is the perfect time to plan a fall getaway to the Hamptons. While many
people associate the Hamptons with summer vacation, the fall season is also a favorite time to visit. The
cool coastal breezes and colorful leaves create the ideal backdrop for exploring the Hamptons’ many
destinations and activities.
So break out your cozy fall sweater … treat yourself to a hot pumpkin-spiced latte … and discover the
beauty that is the Hamptons in autumn.
Wine Tours
There’s no wrong time for a Long Island wine tour, but the fall season is truly special. The cooler
temperatures create the perfect weather for sitting outside, sipping wine and marveling at the scenic
rolling vineyards. There are 3 popular wineries in the Hamptons, but dozens more in the North Fork if you
want to experience the “wine trail.”
The best and easiest way to enjoy a Hamptons wine tour is with a chauffeured limo service. This allows
you and your group to sit back and enjoy the ride safely without doing any driving yourself.
What to know:
- Book your wine tour in advance to ensure the best rates and availability of your preferred vehicle.
- Many wineries require advanced reservations for groups (and group size limits), so be sure to check with each location before you go.
Pumpkin Picking & Hayrides
If you’re looking for family-friendly fall activities in the Hamptons, pumpkin picking is always a fun option.
There are several farms in the Hamptons that allow you to explore the patches to pick your own
pumpkins. Some locations offer additional activities, like hayrides, corn mazes, apple picking and games
for kids. If you just want the pumpkins (without walking through a patch) there are also plenty of
standalone farm stands.
What to know:
- Fairview Farm at Mecox in Bridgehampton is a popular option for pumpkin picking, corn maze and other family-friendly activities, like a corn cannon. Maze opens Labor Day weekend.
- Hank’s PumpkinTown in Water Mill opens Sept. 7 for pumpkin picking, wagon rides, corn maze, giant slides and more.
43rd Annual Montauk Fall Fest
The Annual Montauk Fall Fest is a beloved community event with activities for all ages. Whether it’s your
first time to Montauk (located on the Eastern tip of Long Island), or it’s your favorite spot in the Hamptons,
the Fall Fest is an excellent reason to visit. The event offers live music, inflatable slides, pumpkin painting,
a food tent, beer and wine stands, silent auction and the always-popular Chowder Contest.
What to know:
- The 43rd Annual Montauk Fall Fest (2024) is scheduled for Columbus Day Weekend: Oct 12 & 13, 2024.
- Located in the heart of Montauk, near the Chamber of Commerce at 742 Montauk Highway Montauk, NY 11954
East Quoque Fire Department Seafood & Beer Festival 2024
For the over-21 crowd, this fun yearly event is a favorite among seafood lovers and beer lovers. Hosted
by the East Quogue Fire Department, the festival features live music, fresh local seafood, craft brews and
more. New for 2024, the event will bring “more fun and exciting games and gambling for this year.” The
festival sold out in 2023, so be sure to grab tickets as early as you can. (Must be 21 or older to attend.)
What to know:
- The EQFD Seafood & Beer Festival is scheduled for Saturday, September 21, 2024, from 6-10pm
- Located at 465 Montauk Highway East Quogue, NY 11942
Westhampton Beach Fall Festival on Main Street
This is another popular fall festival in the Hamptons (especially for those that prefer a shorter distance from the city). Located in Westhampton Beach, the annual Fall Festival on Main Street offers great food and family-friendly activities. Foodies especially love the lineup of food trucks, as well as food and beverage tents. The event also has live music, artisan vendors and activities for kids. Plus, it’s centrally located on Main Street, making it easy to explore the many other shops and restaurants in Westhampton
Beach.
What to know:
- The 2024 Westhampton Beach Fall Festival on Main Street is scheduled for October 12, 2024, 11am to 5pm (Rain date 10/13)
- Main Street, Westhampton Beach, NY, from Library Avenue to Moniebogue Lane
Make your fall Hamptons getaway so much easier
Sit back and enjoy your travel while our chauffeurs do the driving. Jackrabbit Limo is a locally operated
black car and limousine service in the Hamptons. We offer transportation to the Hamptons from NYC,
Long Island and all the NYC airports, as well as on-demand Hamptons car service, wine tours, party
buses and more. Call (631) 600-7700 or reserve your vehicle online.