How to Spend 24 Hours in the Hamptons

The weekend before Halloween, we ended up taking a quick and impromptu trip to Long Island. Natty Guy bought a car that was located on Long Island so we made a last-minute decision to fly out to pick it up.

We left early on Saturday morning and flew into Newark (the closest airport we could get into at the time). From there it was a 2 hour Lyft ride to the seller’s house. We picked up the car and by 11:30 AM we were on our way to explore the Hamptons before driving the car back to Ohio on Sunday. Here’s what we did during our whirlwind visit!

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How to Spend 24 Hours in The Hamptons

From the Hyatt Place Riverhead, plan on an hour and a half drive to get all the way out to Montauk. More (much more) if traffic is heavy when you visit.

Sights

Parish Art Museum. Near Southampton, the Parish Art Museum is housed in a contemporary yet rustic building and the dramatic property contains both indoor and outdoor displays.

Montauk State Park & Lighthouse. When you hit the end of the road, you’ll be at Montauk State Park and the lighthouse. Take time to walk around the park and explore the ruggedly beautiful beach. I could have watched the surfers here for hours. The lighthouse is worth a quick walk through and had some interesting displays on the long history of surf casting in the area.

Shopping

If you like to shop, you’re going to like the Hamptons! The three most developed shopping areas are:

Main Street, Southampton has a great mix of shops (clothing, home, accessories, jewelry) and restaurants. For edible treats, be sure to stop at Village Gourmet Cheese Shoppe and Tate’s Bakery for their famous chocolate chip cookies.
In and around Main Street, East Hampton. This area was our favorite of the shopping districts! The stores here are a bit more condensed and contain premium retailers like Golden Goose and Zimmermann as well as national brand outposts like J. Crew and Vineyard Vines.
Division and Main Street in Sag Harbor including its adorable LoveShackFancy showroom.
The Montauk General Store, Balsam Farms Montauk Market, and various other shops along the Montauk Highway.

Beaches

On our tight schedule, we held our beach experience to the one at Montauk. Other popular beaches along the route include:

Sagg Beach in Sagaponack
Egypt Beach in East Hampton (undeveloped, no restrooms/lifeguards)
Wiborg Beach in East Hampton (wide beach, surfers)
Indian Wells Beach in Amagansett
Foster Memorial Beach in Sag Harbor (a bit warmer water than the Atlantic side)

Food/Drink

There are numerous wineries (and pumpkin patches in the fall) located on the drive out to Montauk. Wölffer Estate Vineyard is especially Instagrammable if you can handle the crowds! The only meal we took was lunch. We enjoyed the lobster rolls and corn fritters at The Corner Bar in Sag Harbor but there are plenty of other lobster roll stands along the way. If you’re in the mood for something fancier, the towns of the Hamptons will have something to fit the bill.

Where We Stayed

As the smaller, boutique hotels were either sold out or ridiculously expensive (hello, $1400/night), we ended up staying at the Hyatt Place East End Riverhead. While not in the heart of the Hamptons, it’s situated at a great launching spot for trips to that area as well as the North Fork and its many wineries.

The Hyatt Place is a newer property with a blend of traditional and studio-style rooms, quite a few with views of the quaint harbor right outside. There’s a bar on-site and a handful of restaurants within walking distance. If you’re traveling with kids, the Long Island Aquarium is situated right next to the hotel.

We arrived mid-evening tired from the day and not wanting to hunt for an outdoor restaurant during COVID. The lobby had a great assortment of socially distanced booths, eating and lounge areas, so we grabbed a few local beers from the bar and ordered a pizza via Door Dash for dinner. Quick, COVID-safe, and convenient!

The small harbor outside Hyatt Place East End/Riverhead

The North Fork

With more time, take a drive to the North Fork. It will take about an hour to drive from the Hyatt Place to Orient Beach State Park, the easternmost site of those listed below. Along the way, you may want to stop at:

The Horton Point Lighthouse,
The East End Seaport Museum,
An Antique Carousel in Greenport,
Orient Beach and Orient Beach State Park, and
Numerous wineries along the route!

Be sure to verify business hours before visiting as some sights are still closed due to COVID restrictions.

While we didn’t venture into the city this trip, we enjoyed these quick glimpses of the Brooklyn Bridge and lower Manhattan as we made our way back home on Sunday! For a first-timers guide to New York City, check out this post.