The heart of Bridgehampton’s main drag is a mere .2 miles long — sneeze while you drive by, and you may just miss most of it. Its petite position makes it all the more astounding to see the bounty of independent businesses packed into this sliver of a stretch on Montauk Highway.
European settlers began to creep into the land of Montaukett and Shinnecock Native Americans in the mid-seventeenth century, but it wasn’t until 1699 that the words “Bridge Hampton” appeared in official town records, nodding to its bridge over Sagg Pond as a pivotal link between the areas of Mecox and Sagaponack.
But Bridgehampton is no middle child, as evidenced by this not-even-scratching-the-surface run-down of things to eat, drink, see and do.
Almond, 1 Ocean Road, 631-537-5665. Open year round, owners Eric Lemonides and chef Jason Weiner have managed to achieve both ease and excellence for over 20 years, celebrating and highlighting the bounty of local farmer partners on their market-driven menu. On any given day, you can grab a table in the breezy dining room or a seat at the convivial bar (shout out to bartender Bobby Weissleder!), perhaps next to a local winemaker, artist or author, or perhaps just another hungry soul, and find yourself satiated on a multitude of levels. Next door, their grab-and-go L&W Market is an excellent pit stop for fast sandwiches, soups, coffee and other fuel-‘em-up necessities.
Pierre’s, 2468 Main St., 631-537-5110. A popular haunt for Francophiles and for good reason. This 21-year-old French bistro’s Alsatian namesake owner, Pierre Weber, with his cloud of gray hair and ever-present Provençal-pastel pants, is always around. If there’s bouillabaisse on the menu, get it; the silky, saffron-spiked seafood-strewn dish is dynamite. If you’re just strolling by, duck into the petite café next door, where Weber’s past as a baker is in full glory. Order a macchiato and a light-as-air, fist-sized coffee meringue (you’re welcome).
Dopo il Ponte, 2402 Montauk Highway, 631-536-6006. Since they opened in the spring of 2022, this wood-fired, al fresco Italian eatery filled the gaping pizza hole left by World Pie’s departure. The sister spot of Southampton’s Dopo Argento and East Hampton and Sag Harbor’s Dopo la Spiaggia, expect individual-sized, crispy crust, wood-fired pizzas and heartier traditional pastas and primi piatti, like veal scaloppine, along with local-leaning dishes like breaded flounder with pistachios, capers and Champagne mustard sauce.
Bridgehampton Candy Kitchen, 2391 Montauk Highway, 631-537-9885. Open since 1925, the Kitchen is a beloved hold-out of how it used to be, filling bellies with diner classics like frothy egg creams and their excellent club sandwich, generously yet neatly piled with juicy turkey and just-right crispy bacon. There’s homemade ice cream, too, all the better spooned while tucked into one of their sweet little blue booths or at the white Formica counter. Owner Gus Laggis bought the Kitchen in 1981, and you’ll still find him and his family here, ringing up customers with a smile seven days a week.
Elaia Estiatorio, 95 School St., 631-613-6469. Just off Main Street around the corner from the Candy Kitchen sits this lovely intimate little Greek restaurant, owned by Chris Boudouris and Sofia Crokos. Flavorful and oh-so-very fun, it’s the kind of place you want to be a regular, as much for the friendly atmosphere as for the authentic, elevated Greek dishes, thoughtful cocktails and solid wine list (no surprise, as Boudouris also owns and curates Bridgehampton Wine Cellar).
Tapovana Lunch Box, 2368 Montauk Highway, 631-537-2806. Corey De Rosa opened the ayurvedic-focused Tapovana Healing Center in Sag Harbor in 2006. Since 2021 he’s added feeding the body as well as the soul with this, the Lunch Box, located inside the stately, white-pillared Bridgehampton Community House. Hours are limited (Monday to Friday, 11:30 a.m. to 2 p.m.) and there are only a couple of wee café tables for sitting, but the daily-changing vegetarian-skewed South Indian-inspired dishes are worth the hustle.
Bobby Van’s Steakhouse, 2393 Montauk Highway, 631-537-0590. Open all year, this storied steak slinger has been in business since 1969. At times the haunt of martini-sipping authors and artists (although don’t believe the tale that Truman Capote finished In Cold Blood here; good story though it is, that novel was published in 1966), today it remains the master of meat, great service and stellar steakhouse faves for indoor or al fresco eating. 2393 Montauk Highway, 631-537-0590
Golden Pear, 2426 Montauk Highway, 631-537-1100. The third of four incarnations of this Hamptons-founded café, the crowd-pleasing Pear offers early-bird service seven days a week, starting every day at 6:30 a.m. with good, hot coffee, eggs of the omelet and scrambled selections, and locally themed sandwiches and wraps, like the aptly named Bridgehampton — citrusy tuna salad with grated carrots and sliced cucs on whole-grain ciabatta bread. Grab a sunny sidewalk table and make your plans for the day.
Sundaes on Main. 2414 Main St., 631-488-7592. Happy first anniversary, Sundaes! Owner Jeanie Strong is as welcoming and sweet as the soft-serve froyo, sorbet and — as of May — ice cream she sells in flavors like Montauk Mint, Southampton Salted Caramel and Bridgehampton Batter. There’s an abundance of toppings, a back room full of 70 lever-served candy chutes plus every package candy from your childhood you can imagine. Closed Mondays.
The Hampton Library at Bridgehampton, 2478 Main St., 631-537-0015. Book lovers have been getting their fix here since 1877! But despite the 41,000 tome-strong selections, there’s more here to check out, like author readings, a weekly knitting and crochet circle, tai chi, writing workshops (get moving on that novel this summer!), ESL classes and so much more for the curious mind.
White Room Gallery, 2415 Montauk Highway, 631-237-1481. If you generally hesitate to poke your head into art galleries, fearful of judgy black-clad art experts, the White Room is chock full of pop-art fun. Owner Andrea McCafferty fills her wall with provocative, fun works from artists like Philippe le Closier, Reisig and Taylor and Markus Klinko, as well as eye-catching outdoor sculpture garden.
Lucille Khornak Art and Photo Gallery, 2400 Montauk Highway, 888-858-1827. Known for her portrait photography, Khornak’s array of local and far-flung shutterbug friends often grace the light-strewn walls of this airy gallery, in ever-changing exhibits throughout the season. She also teams up with Andrea Bejsovec of ABI Fine Art, whose shows focus on local artists and their depictions of life on the East End.
Waves, 1 Main St., 631-537-7767. Owner Ariana Li grew up around the playful yet classic dresses, tops and bathing suits at her mother’s iconic Hamptons shop, which opened in 1980. Now at the helm, she carries on her mom’s flair for fashion, with brands like Cara Cara, Ciao Lucia and CP Shades.
Leallo, 83 Main St., 631-808-3414. Megan Chiarello’s love letter to a life lived comfortably on the East End manifests in her lifestyle brand of clothing. Here in the Bridgehampton shop, you’ll find the softest, cuddliest cotton and cashmere casuals, in muted tones of soft pink, blue, gray and tan, along with classic white and black.
L’Epicuriste, 2466 Montauk Highway, 631-899-4900. This knowingly curated gourmand’s paradise has everything you never knew you needed, like Moroccan-inspired Villa Jerada spice mixes, brightly colored, handmade dishes from Porta, sleek Gharyan stoneware and hand-dipped candles to set the mood, along with a petite selection of cheeses and meats, too.
Dog & Co., 2491 Main St., 646-450-8518. Not only does owner Mindy Montney provide adorable assets for your four-legged friends, she also has her own line of canine coats and accoutrements to make your pup the most stylish in the rain, sun or snow. She also offers an excellent selection of treats, several of which are South Fork-centric brands.
Churchill Wines & Spirits, 2489 Montauk Highway, 631-537-0287. David Churchill’s spirited store has all the classics for wine lovers, plus an abundance of rosé right up front, but its his super-fun spirits selection that we get jazzed about, carrying bottles from local darlings Sagapanock Farm Distillery to a dialed-in selection of Italian vermouths and amari. And if he doesn’t have it the bespoke bottle you seek? Ask. He’ll get it.
The Exchange Thrift Shop, 2350 Montauk Highway, 631-377-0469. When St. Ann’s Church closed their opportunity shop, Leslie Handley-White picked up the reigns to fill a need for the area’s budget-hemmed residents, and she does an amazing job. This shop is full of gems from the attic, both vintage and more recent. Here, you’ll find gently used threads from brands like J. Crew and Saks Fifth Avenue, along with fun purses, hats, dishware, jewelry and so much more. And if you like, you can drop off clean donations, too, in the cute little wagon right in front.
Topping Rose House, One Bridgehampton–Sag Harbor Turnpike, 631-808-2000. This majestic Greek revival building, built by Abraham Topping Rose in 1842, got a super spiffing up (including the addition of a pool) about a decade ago, and is now the site of a luxurious inn and restaurant, helmed by famed toque Jean Georges Vongerichten. The rooms nod to the past while staying firmly in the modern-amenity present, with Frette linens, Matouk towels and Southampton Soap Company bath bounty, among other guest niceties.
Bridgehampton Inn & Restaurant, 2266 Montauk Highway, 631-537-0553. This stunning circa 1795 clapboard inn sticks to the building’s historic character, with pretty four-poster beds, old-fashioned quilts and antique dressers to bring you back to days gone-by. There’s also a charming on-premise restaurant (and as the Inn is owned by the folks from Loaves & Fishes, you can bet you will dine very, very well).