Things To Do

Wölffer Estate Vineyard

Nice to stop here on your way TO or FROM East Hampton. Get the cheese plate. Make sure to make a reservation if you’d like to do a tasting.

Village of East Hampton

Take a morning or afternoon to do some window shopping in town. There are some incredible stores. Ralph Lauren has three stores, each with a different vibe. There are some fun coffee shops around. The book store is always fun to browse, especially the local author selections. Some of Kerry’s suggestions: JCrew Restoration Hardware Stony Clover Reformation Ralph Lauren (all!) Chanel, Prada, Valentino Breezin' up Veronica Beard LVIS

Main Beach

Two village beaches waive the $50 per day parking fee after September 15th; Main Beach and Two Mile Hollow Beach. ALL other beaches require a parking permit 365 days a year.

LVIS - The Ladies’ Village Improvement Society

Best thrift store in the Hamptons!

Breezin' Up

Villa Italian Specialties

Favorite go-to for all things Italian! Subs, sandwiches, family style meals, etc.

Hampton Chutney Co. - $$

This is Sir Paul McCartney's favorite place to eat in the Hamptons. Any place that works for a vegetarian Beatle works for me :-)

Hampton Eats

Serving seven local foodie favorites from one space, vendors include Villa Italian Specialties (in EH Village), Montauk Bake Shoppe, Beach Bakery & Grand Cafe (in Westhampton Beach), Stuart’s Seafood (in Amagansett), and Paul’s Pizza (in Southampton Village).

Moo Moo Ice Cream

Ice Cream! Need we say more?

Carissa's the Bakery - Amagansett

Jack and Kerry love to stop here for a pastry before morning walks on the beach.

Rita Cantina

CLOSE TO WELCOME PARTY AND WEDDING RECEPTION. Good dinner option close to bay beach for sunset viewing! Happy Hour 4-6.

Bostwick's on the Harbor - $$$

CLOSE TO WELCOME PARTY AND WEDDING RECEPTION. Great dinner option with a good view of the sunset.

Springs Tavern and Grill - $$

CLOSE TO WELCOME PARTY AND WEDDING RECEPTION. Great, low key, family friendly, affordable tavern.

Gerard Drive

Beautiful street surrounded by water. Our family drives this at least once each trip!

Amber Waves Farm, Market & Cafe - $$

Most expensive grocery store in the Hamptons but their baked goods are unreal.

The Stephen Talkhouse

After Party Spot - Bar in Amagansett

La Fondita - $$

Best place to grab tacos to eat on the beach!

Rowdy Hall - $$

Who wants a burger and a beer?

Jack’s Stir Brew Coffee - $$

Coffee spot - You may spot a celeb or two here!

Cavaniola's Gourmet Cheese Shop

BEST CHEESE EVER!

il Buco al Mare

A simple, relaxed menu presenting the best local seafood & produce. Featured items include ancient grain focaccias, imported tinned fish from the Iberian Peninsula and Italy and seasonal local fare from our wood burning oven.

Clam Bar at Napeague - $$

The Clam Bar. Over the last 43 years, the Clam Bar at Napeague has cemented itself as an institution, and a landmark in the Hamptons. East of Amagansett, west of Montauk, on the highway.

LUNCH Lobster Roll - Amagansett - $$$

An institution.

Balsam Farm Stand

Fresh fruits and vegetables. Our go to farm stand for corn all summer.

Cavaniola Gourmet Cheese

Cheese, glorious cheese!

Big Olaf

Grab a cone and stroll by the yachts.

Shadmoor State Park

Just shy of 100-acres of preserved land, this park has spectacular views of the ocean from the bluffs. This 2.5-mile loop trail which is considered 'easy' takes an average of 51 min to complete.

Walking Dunes Trail

Amazing trail to walk!

Montauk County Park

Pretty walk around the water in Montauk - bay side.

Montauk Fall Festival and Chowder Contest

No entrance fee. 11 a.m.-5 p.m. Oct. 12-13 This event includes an annual Clam Chowder contest (Saturday only), Farmers Market vendors, kid’s activities, local band performances, yummy eats, fall themed activities, beer and wine, a silent auction, and more! Both Saturday and Sunday will include live music from 2pm to 5pm.

Montauk Brewing Company

Montauk Brewing Company was started in 2012 by a few surfers who had figured out how to make beer while in college and all happened to grow up in Montauk. In 2022, Tilray Brand’s acquisition of Montauk Brewing Co. closed for an initial purchase price of $35.11 million. Visit the Montauk Tasting Room and enjoy the flavors.

Gosman's Seafood

Head to Gosman’s for seafood, ice cream or just a drink with a view. One of the few places you can access a bay beach for free. There is a fun fish market and some shops there too! You’ll also find some great restaurants in this area. Unparalleled views.

Hideaway Montauk

Casual dockside mexican food by a few montauk amigos.

The Montauket

Dinner, sunset, live music!

Montauk Lighthouse

The end.

One Stop Market - $

Small market with excellent meats, sandwiches and hot bar.