Southampton, NY Fall Weekend Itinerary

Southampton is one of my favorite towns in the Hamptons — and it really shines in fall.

Think crisp ocean air, cozy coffee shops, pumpkin stands, and downtown shops decked out in fall decor. Whether you’re apple picking, sipping cider, or strolling the beach in a warm sweater, there’s no shortage of autumn things to do here.

I lived in the Hamptons for a year and regularly return to visit family, I put together this Southampton fall weekend itinerary based on some of my favorite things to do here!

Note: There is the Town of Southampton, which encompasses a number of hamlets throughout the Hamptons, and the Village of Southampton. This itinerary covers things to do in and around the Village of Southampton.

Store front decorated for halloween and fall. Shopping Main Street in Southampton, Southampton, New York, The Hamptons. — Southampton, NY fall weekend itinerary

White flowers in foreground with background of marshland turning brown and bright red, with calm ocean in background on gloomy fall day. Fall on Meadow Lane, Southampton, New York, The Hamptons. — Southampton, NY fall weekend itinerary

Southampton, NY Fall Weekend Itinerary

Day 1

Grab Coffee & Browse the Shops in Southampton

Start your weekend with a walk through downtown Southampton.

The tree-lined streets and red-brick sidewalks are especially beautiful in the fall, and there’s a nice mix of local boutiques, upscale home stores, and historic buildings to explore. Be sure to pop into Hildreth’s Home Goods — it’s been around for over 180 years and is one of my favorite spots for a good browse (take your time here, the place is deceivingly large!).

For coffee, Kelly’s Cafe, Golden Pear, Four Oaks, and Hampton Coffee Company are solid options in Southampton.

Decorative pumpkins and plants in front of storefront display of women's fashion. Loveshackfancy, Southampton, New York, The Hamptons. — Southampton’s Main Street in fall

Option 1: Coopers Beach

If the weather is nice, head to Coopers Beach in the afternoon. This is one of the most beautiful beaches in the Hamptons, and even in fall, it’s a peaceful place for a walk by the ocean.

Bring a hot drink, bundle up, and enjoy the wide stretch of white sand — you might even spot dolphins or whales in early fall.

A beach parking permit is typically required through mid-September — after that, visiting gets much easier! If you’re heading to the beach during permit season, expect to pay $55 for a day pass — and Coopers Beach is one of the few that even offers them. Once non-permit season begins, parking will be very easy (and free!).

To skip the parking hassle altogether, consider biking, walking, or getting dropped off. Remember, parking requires a permit, but the beaches themselves are free and open to everyone.

0egulations can change from year to year, so be sure to check the latest rules at Southampton Beach Parking Permits before you go. Also, your hotel will likely have up-to-date beach access information.

Option 2: Parrish Art Museum

If it’s cold or rainy, check out the Parrish Art Museum instead. Located just outside the village, this striking modern museum is home to both contemporary and classic works, with a focus on artists who’ve lived or worked on the East End. It’s quiet, spacious, and a perfect cozy activity for a fall day.

Southampton Arts Center is another good option located right in the center of the Village. Or, if you’re up for a drive, schedule a tour at the Pollock-Krasner House (I love this spot!) — tours usually go through October.

woman browsing art gallery modern building Parrish Art Museum southampton water mill new york the hamptons — Parrish Art Museum

Woman standing on wide sidewalk under long awning, alongside field of grasses and trees. Parrish Art Museum, Southampton, New York, The Hamptons. — Parrish Art Museum

Visit A Vineyard

Spend the late afternoon wine tasting at Duck Walk Vineyards in nearby Water Mill, just a few minutes from the village.

The grounds are beautiful in autumn, especially with the vines turning golden. It’s the perfect place to sip a glass of Sauvignon Blanc and ease into the weekend, and they often have live music on weekends (check out the upcoming schedule at Duck Walk Vineyards Events). Best of all, there’s a spacious indoor space for chilly days.

Alternatively, check out nearby Wölffer Estate Vineyard, just a short distance away in Sagaponack. Wölffer Estate Vineyard does sunset live music at the Wine Stand on weekends throughout fall (find the schedule at Wölffer Estate Happenings). It’s not as crowded as summer, but the vibes are still great. Just be sure to bring warm layers, it cools off quickly in the evening! They also have an indoor tasting space, but you’ll need to reserve a table in advance.

Woman in indoor tasting room holding glass of wine with large barrels of wine stacked against wall in background of warehouse-like room. Duck Walk Vineyards, Water Mill, New York, The Hamptons. — Duck Walk Vineyard to the left, Wölffer Estate Wine Stand to the right

Couple smiling at wooden table with stemless wine glasses on grey cold day, background is a vineyard and grass lawn. Wine Stand at Wolffer Estate Vineyard, Sagaponack, New York, The Hamptons. — Duck Walk Vineyard to the left, Wölffer Estate Wine Stand to the right

Grab Dinner

Some popular dinner spots in Southampton include:

T Bar Southampton (Steak & upscale American)
Namiro Sushi (Sushi)
La Parmigiana (Casual Italian, great for comfort food)
Le Charlot (Chic French bistro)

Want to stay in? For premade or take-and-bake meals, Citarella or Farm & Forage have great options.

Day 2

Brunch

Start off day 2 with a big brunch.

If you’re staying in the village and want something walkable, try 75 Main for classic brunch fare and people-watching right on Main Street (this is a really popular spot, try to come early!).

Sip N’ Soda is also a fun spot in the village, it’s an old-school diner that’s been a Southampton mainstay for over 60 years.

If you’re looking for a quick option, check out Ted’s East End Market, Tate’s Bake Shop, or Kelly’s Cafe & Bakery instead.

sip n soda diner southampton new york the hamptons — Southampton’s Sip ‘N Soda

Apple Picking & Pumpkin Picking

Spend your morning out on the farm at Hank’s Pumpkintown or The Milk Pail U-Pick Farm. Both are family-run favorites, and each offers apple picking, pumpkin patches, cider, and fresh baked treats.

Hank’s has more activities if you’re visiting with kids, while The Milk Pail has killer doughnuts and cider.

Apple season typically runs from early September through late October.
Pumpkin season usually peaks from mid-September through Halloween.

Note: Lines can get quite long at both spots on weekends, so try to visit as early as possible.

If you’re looking for more fall things to do, check out Fall In The Hamptons: Top Things To Do.

Large, red barn with painted sign reading "Hank's Hard Cider", barn is surrounded by two tress losing their leaves, picnic benches and farm in near distance on sunny, cold day. Hank's Farmstand, Water Mill, New York, The Hamptons. — Hank’s Pumpkintown

woman selecting pumpkins at hanks pumpkintown southampton water mill new york the hamptons — Hank’s Pumpkintown

Option 1: Southampton History Museum

If you’re up for a mellow afternoon, stop by the Southampton History Museum, just behind Main Street. This cluster of 19th-century buildings recreates what the village looked like 200 years ago, and it’s a great way to get a sense of the area’s past.

They’re open through November and free to the public. It’s also supposedly haunted, so fall is the perfect time to visit.

Option 2: Explore A Neighboring Hamlet

Prefer to check out the surrounding hamlets? There are so many cute towns near Southampton, these are a few of the most popular.

East Hampton – Known for designer shops and big homes, plus an abundance of art galleries and museums.
Sag Harbor – Beloved for their picturesque Main Street, well-preserved architecture, whaling history, and charming harbor. Read more at Sag Harbor Day Trip Itinerary.
Bridgehampton – One of the closest hamlets to the Village of Southampton, known for upscale boutiques, art galleries, and sprawling horse farms.
Montauk – The most California-esque beach town in the Hamptons, it’s got a serious surfer vibe and the oldest lighthouse in New York, Montauk Point Lighthouse. Read more at Montauk Day Trip: Everything To Know.
Shelter Island – Not technically in the Hamptons — but very close by — this is the most secluded spot around, getting here requires a short ferry ride. Upon arrival you’ll find yourself engulfed in solitude — especially in fall!

White shingled buildings covered in ivy turned bright red in fall, shopping area on Main Street in Sag Harbor on sunny fall day. Main Street, Sag Harbor, New York, The Hamptons. — Sag Harbor & Montauk

Shingled building covered completely in lush ivy turning orange and red during fall on sunny day. Main Street, Sag Harbor, New York, The Hamptons. — Sag Harbor & Montauk

Grab Dinner

Close out the weekend with a cozy dinner at:

Southampton Publick House (Laid-back American pub, also has live music)
Saaz Indian Restaurant (Indian comfort food – not your typical Southampton vibe but the food is very good)
Cowfish (Steakhouse on the water in nearby Hampton Bays)

Or, if you spent the afternoon exploring another hamlet, grab dinner there! Sag Harbor and Bridgehampton both have a wide variety of delicious restaurants, East Hampton has lots of upscale eateries, and Montauk has excellent waterfront options.

Where To Stay In Southampton In Fall

Southampton Village has surprisingly few hotels and most are of the boutique variety, you won’t find any chain hotels here.

This time of year you’ll find better availability and guest rooms at lower prices than the high season — definitely a large perk of visiting during the fall months!

A few popular hotels in the Southampton include:

The 1708 House ($$$) historic hotel in central location.
Southampton Inn ($$) largest hotel in Southampton, with plenty of amenities and central location.
Hamlet Inn ($) casual hotel with solid amenities list, located just outside the Village.

For more, check out my guide to the Best Hotels In Southampton, NY.

Southampton Weather In Fall

Fall weather in the Hamptons is fairly mild. This time of year sees ample sunny days with about 7 days of rain per month.

It is, however, hurricane season. Even if the area isn’t directly affected, an East Coast hurricane can cause days of heavy rain throughout the region.

Below are the average monthly temperatures for fall in the Hamptons:

September – 73° / 56°F (High / Low)
October – 63° / 45°F
November – 53° / 37°F

What To Wear In The Hamptons In Fall

Fall fashion in Southampton is like any other time of year: coastal and effortlessly chic. Think elevated casual with a cozy twist — the kind of outfits that look just as good strolling Main Street as they do at a vineyard or pumpkin patch.

Southampton leans more polished and put-together than other Hamptons hamlets — you don’t have to go full city-style, but upscale casual is common here.

And remember, fall sees cold mornings and evenings, so layers are key!

Below are a few ideas of things to wear:

For Daytime Activities:

Lightweight sweaters or cardigans
Long-sleeve blouses or button-ups
Dark denim or casual trousers
Comfortable sneakers or ankle boots (perfect for walking downtown or visiting farms)
A denim jacket or lightweight trench coat for layering
Don’t forget a tote or crossbody bag — handy for carrying farmstand finds or your vineyard souvenirs.

For Evenings Out:

A chic sweater dress or elevated knit top
Leather or suede boots
Midi skirt with a tucked-in blouse
A wool coat or structured blazer
Optional: a scarf or additional layer for outdoor dining

Beach & Nature Outings:

Windbreaker or light puffer
Leggings or joggers for beach walks
Beanie or ball cap
Sunglasses (yes, even in fall!)
Waterproof boots if you plan to hike or explore sandy dunes

Getting To Southampton

By Car

The Hamptons are located at the tip of Long Island’s South Fork, a straight shot from New York City.

The drive to Southampton normally takes about 2+ hours (about 100 miles from NYC). Fortunately, Southampton is on the western edge of the Hamptons and a little quicker to get to than other hamlets.

For more information, head on over to How To Get To The Hamptons.

By Bus

One of the most convenient ways to get across Long Island is via the Hampton Jitney. These are luxury buses with cozy seats, wifi, restrooms, and an attendant.

Tip: For even more space check out their luxe option, the Hampton Ambassador.

By Train

The Long Island Railroad (LIRR) combines convenience and affordability.

The route takes 3 hours so this is especially a great option when the roadways are jammed with cars.

The train continues from Penn Station to Montauk with a transfer at Jamaica Station or there’s an express option with less stops (the later of which is seasonal). Stops in the Hamptons, in order from west to east, include: Speonk, Westhampton, Hampton Bays, Southampton, Bridgehampton, East Hampton, Amagansett, and Montauk.

By Air

For the quickest (and least affordable) option, BLADE offers helicopter service into East Hampton during fall.

Think airline gone helicopter, it may be pricey but it’ll get you to the East End in a fraction of the time.

Getting Around

If planning to stay in the village of Southampton, it’s easy to get around by foot and utilize ride share or bike rentals when needed.

If you aren’t able to stay right in the village, or you plan to explore nearby towns, a car will be necessary.

Large white home with black shutters, neat green lawn, well manicured bushes, and large, mature tree towering over home. Rogers Mansion, Southampton History Museum, Southampton, New York, The Hamptons. — Southampton History Center

A weekend in Southampton is the perfect fall getaway! This time of year is so charming and thanks to smaller crowds, it’s much more chill than summer.

I hope you’ve found this helpful in planning your trip and have the best time!

For more ideas and information, check out my additional Southampton and Hamptons guides below.

Southampton, NY Fall Weekend Itinerary