How to spend an affordable weekend in The Hamptons

The South Fork of Long Island is known for being a haven for affluent New Yorkers and celebrities fleeing the city in search of fresh farmland and Oceanside views. After a weekend road-tripping through this region, to my surprise, I realized that there were a ton of activities to do in the eastern hamlets and villages of Long Island that are accessible for the average explorer.

Only an hour and a half from New York City, Westhampton is the perfect spot for those looking for more affordable accommodations. If you are hoping to experience The Hamptons like a local, your best option is to find a vacation rental property online with a group of friends. If you have the chance to travel during the “off-season”, to your advantage many of the properties are available for short-term weekend rentals (instead of a full week) with rates that are often lower then in the summer peak periods. Lucky for you, this area of Long Island is just as beautiful in the autumn.

What to do in The Hamptons

The best way to see the South Fork is by taking the time for leisurely drives along the coast and through the farmlands. Begin by taking a drive down the Montauk Highway to visit the Westhampton Farmers Market Farmstand. Every day, they sell an assortment of produce, freshly baked Blue Duck Breads and baked goods, cheeses from nearby farms and other jams and spreads for locals and visitors to enjoy.

Travel up Montauk Highway on Route 27 East to explore The Hamptons Wine Trail. For those visiting The Hamptons in the fall, plan your harvest season routes to see the changing leaves while sipping and savouring some of the bountiful wines from nearby Long Island vineyards. While there are over 60 vineyards all over Long Island, South Fork favourites include Duck Walk Vineyards, Channing Daughters Winery, Wolffer Estate Vineyard and The Grapes of Roth.

Many of the local shops and restaurants are along Main Street in Westhampton Beach. Be sure to also save some time to take the scenic drive along Dune Road to see the rows of beachfront McMansions along the Atlantic shores.

Continue your scenic drive along the Montauk Highway passing through the affluent area of East Hampton. Take your time driving to catch glimpses at the quintessential Americana houses along the way. Escape the fresh fall winds by exploring a local gallery or plan your visit around a local art fair. The Hamptons Art Hub is a great resource to learn about the arts and cultural activities going on.

Where to Eat in The Hamptons

While there is plenty along the Main Street stretch, all of the locals we spoke to recommend heading over to John Scott’s Surf Shack for a cool drink and the catch of the day. Known for their delicious steamers, lobster rolls and wing night; John Scott’s Surf Shack is well-loved for their hearty meals and laid back atmosphere.

Be sure to also drop by Brewology295 for some of the best craft brews in the area. Pairing small-batch craft beer with fresh food made with local ingredients; this gastro-pub playfully displays what is currently on tap on a periodic table allowing guests to sample seasonal brews. Brewology295 is open nightly for dinner and for brunch on weekends.

What to do in Montauk

However, if you’re looking for more of a vibrant waterfront stretch, head over to Montauk for the weekend. At the end of the road, you’ll reach the easternmost point of Long Island where you’ll find this surfer‘s paradise. Home of six State Parks, and known for their local fisheries, Montauk exudes a youthful energy that is worth exploring. For an artistic and upbeat vibe, visit Surf Lodge nestled on Fort Pond Bay for delicious eats at their onsite restaurant, to hang out at their open-air deck or to stay in one of their 32 waterfront rooms. Or, for those looking for something more luxurious, swing by the Montauk Yacht Club to stay at a resort oasis with three pools, four tennis courts, a spa, and a marina.

All images in this article were taken with the Nikon DSLR D5500.