4 Blocks on the East End Where You Can Eat, Shop and Spend the Whole Day

We could easily spend our entire summer lounging by the pool, but that would be a shame: The East End is full of charming, walkable nooks just waiting to be explored. From brunch to window-shopping to cocktails, these four blocks have all the ingredients for a dreamy day.

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Sag Harbor: Main Street Between Washington Street And Long Wharf Village Pier

On the outskirts of downtown Sag Harbor you’ll find a refreshing, low-key vibe by the pier.

Eat: It’s not really a day in the Hamptons without a lobster roll. Local favorite Dock House is known for its lobster rolls, clam strips and fried scallops. Get your order to go, snag a seat on the dock and watch the world go by. Hopefully you saved room for dessert, because practically next door you’ll find Big Olaf and the best waffle cones around.

Shop: Stroll down the wharf to Main Street and pop into the cozy Harbor Books. The well-stocked shelves and friendly staff make it impossible to leave without at least one new beach read. Afterward, stop into Matta for breezy, globally sourced clothing (think embroidered caftans and printed sarongs). 

Do: If you thought to invite your four-legged bestie on this excursion, wander down the pier and find a spot on the small sandy patch of beach next to wharf (it’s leashed-dog friendly). Not feeling the beach? Head to the Bay Street Theater for an afternoon show.

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Montauk: South Edgemere Street Between Embassy And Essex Streets

Skip the crowds at the beach and head to this stretch in Montauk for a workout followed by local brews.

Eat: Pick up a focaccia sandwich or a salad at Primavera Pizza and then walk over to Montauk Brewing Company for a summer ale.

Shop: You never know what you’ll find at Vintage Pink, but we bet at least one thing will go home with you. The eccentric shop is full of gift items such as antique jewelry, vases and more.

Do: Hit up SoulCycle’s Montauk outpost for a workout (preferably before having those beers).

Mattituck: Love Lane

Go for the name, stay for the charm. On the North Fork, Love Lane is the perfect complement to an afternoon of wine tasting.

Eat: Whether you go for breakfast, lunch or dinner, Love Lane Kitchen has a seat for you. (At breakfast, you definitely want the stuffed French toast.) Or, for a quicker option, head next door to Lombardi’s Love Lane Market, where you can grab a sandwich, salad or slice of pizza at the counter. Craving something sweet? Make sure to stop in Love Lane Sweet Shoppe, which is full of classics like Necco Wafers, Charleston Chews and Pop Rocks.

Shop: Pop into Mint and just try not to buy all its dreamy floral dresses before heading to the Village Cheese Shop to sample and select some cheeses for your next beach picnic.

Do: Sink into the comfortable leather chairs at Roanoke Vineyards Wine Bar and have a flight of Roanoke Wölffer Estate wines.

Southampton: Main Street Between Route 27 And Meeting House Lane

Round up your besties for brunch followed by window-shopping in this corner of Southhampton.

Eat: Begin your day with a slice of fruit pie and coffee at Blue Duck Bakery Cafe (hey, you’re on vacation—sour cherry pie is an acceptable breakfast food). Not feeling the sweets? Grab a cappuccino or an Aperol spritz and avo toast at Sant Ambroeus.

Shop: Search for your next beach read at Southampton Books, dig for treasures (and there are plenty) at Collette Luxury Consignment or stock up on workout gear at Bandier.

Do: Spend the rest of the afternoon strolling around the Southampton Historical Museum, which is actually a complex of 12 historic buildings, including the Greek Revival Rogers Mansion (built in 1843).

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