I was inspired to do this post after someone sent me a message via Facebook asking for info on things to do during a weekend trip to the East End of Long Island. I really had to scratch my head on this one. A fun weekend in the Hamptons for me usually consists of a laying on the beach with a good book, or in my hammock with an ice cold Angry Orchard hard cider. I’m pretty low maintenance in the Hamptons.
Once you make it through the traffic – you will be hungry. At Duckwalk Vineyards you can purchase bread and cheese and eat on their lovely patio overlooking their vineyard. Heading east, art lovers should explore the new Parrish Art Museum in Water Mill.
After you settle in at your hotel or vacation rental, take a stroll through downtown Sag Harbor. Burger aficionados will enjoy LT Burger, well known in the village for their decadent milkshakes. History buffs should place The Sag Harbor Whaling & Historical Museum on their “must see” list. Sag Harbor is known for being an enclave for artists and writers. Harbor Books carries a wide selection of books for people of all ages and interests. Don’t forget to ask about any readings. They are usually free and feature top notch writers.
If you love shopping, check out the fabulous stores in East Hampton. While you’re there, catch a flick at the cinema on Main street. After the movie, you can feed your sweet tooth at Dylan’s Candy Bar. Yard sales and antiquing are very popular in the fall. Pick up a copy of Dan’s Paper and The Independent (both are free and often found in supermarkets) to find listings of sales.
If you need a good workout, try SoulCycle (think cycling and dancing; it’s popular, so sign up early) or my favorite alternative – a vigorous walk/run down a local beach. After you’ve burned off those calories, head down to Amagansett for some seafood at Lunch/Lobster Roll. Keep going east on Route 27 to beautiful Montauk. Stop at the lighthouse and take in the view. If you’ve made it this far, stop by Gurney’s Resort and Spa for a massage. (Insider tip: Book ahead, take the Long Island Railroad to Montauk and ask for complimentary car service for pick up and drop off).
36 hours may not be enough time to enjoy a lot of these venues, but I guarantee you will have fun trying!
When is the best time to go? – Now. Hotel rates drop significantly after Labor Day.
Where should I stay? – There are lots of options. Hotels, B &Bs, vacation rentals. (Insider tip – Stay in Riverhead. You will save a bundle and will be 30 minutes away from the Hamptons.
Do I need a car? – That depends on where you stay and what you want to do. The Long Island Railroad and Hampton Jitney provide rail and motorcoach service, respectively. There are taxis available but you’ll have more flexibility and less downtime if you have a vehicle.
If you have a favorite thing that you do in the Hamptons, let me know in the comments section.