Sag Harbor has become the Hamptons hamlet where everybody wants to be. With nearly every amenity centrally located within the waterfront downtown business district, it’s during the late spring and summer months when it’s truly hustling and bustling. Consider this your guide to this old whaling village’s good food, unique shopping and creative entertainment.
The aptly named Estia’s Little Kitchen (1615 Bridgehampton-Sag Harbor Turnpike, 631-725-1045) is first come, first served and fills up fast for its crowd-pleasing Mexican-American fare, serving both breakfast and lunch six days a week, and dinner Friday and Saturday. If you do get stuck waiting, be sure to grab a mimosa: Freshly squeezed OJ and super dry bubbles served in a goblet. The best in town.
Family owned and operated, the Cove Delicatessen (283 Main St., 631-430-6708) sits just past Otter Pond on your way into town. For decades, they’ve featured homemade German-style deli fare and a Boar’s Head-centric slew of specialty sandwiches available for both breakfast and lunch. Check out their recently added al pastor tacos (available from 11 a.m. to 2 p.m. only). Game-changing.
Just beyond the fork on Madison Street is Il Capuccino restaurant (30 Madison St., 631-725-2747). Chianti bottles hang from the ceiling while Dean Martin plays in the background. It’s warm, it’s welcoming, it’s old-school classic Italian comfort food. Don’t refuse the bread basket, for these housemade garlic knots are the star of the show.
Page at 63 Main (63 Main St., 631-725-1810) is a Sag Harbor mainstay, serving refreshed classics as well as uniquely modern dishes daily for lunch and dinner. This local favorite has a bustling bar and a unique aquaponic-clad atrium in the back. Brunch is available on the weekends. Get the crispy fried calamari with a glass of Sancerre and people watch.
Open for lunch and dinner, the wood-fired grill at the center of Mediterranean-chic Lulu Kitchen and Bar (126 Main St., 631-725-0900) elevates the usual culinary suspects, but the flame show isn’t for meat only: Lulu has plenty of vegetarian options. The faint yet pleasantly constant murmur around the room adds an extra dose of conviviality to this eatery.
K Pasa (2 Main St., 631-800-8226) delivers solid Mexican fare from breakfast to dinner, offering specialty tacos for $6 each, as well as salads, rice bowls, chips and dips, birria and ceviche. The spicy snap of their margarita is delightful, made with jalapeño-infused tequila and a homemade togarashi rim, as is their ample list of sustainable tequilas, mezcals, beer and wine.
Chef and restaurateur Laurent Tourondel’s LT Burger may be gone, but his second Sag Harbor enterprise, Sag Pizza (103 Main St., 631-725-3167), serves burrata, seared octopus, handmade pastas and gelato at this bright, cheerful staple. The crispy Neapolitan-style personal pizzas cooked in a wood-fired oven feature fresh ingredients with a near perfect ratio of sauce and cheese.
Smack dab in the middle of town is Sag Harbor Cinema (90 Main St., 631-725-0010). Illuminated by the restored, iconic neon red “Sag Harbor” sign on the front of the building, everything from new blockbuster releases to old Hollywood classics and independent films grace its silver screen. Ticketholders can pop upstairs to the theater’s Green Room, a lively rooftop bar and outdoor deck.
For over 30 years now, Bay Street Theater (1 Bay St., 631-725-9500) has hosted concerts, benefits, comedy shows, dramatic plays and dance performances year-round. Seating nearly 300, the theater doubles as a community cultural center, offering beginner salsa instruction, classes in acting, improv and voiceover and weekly summer-long workshops for kids.
Formerly a Methodist house of worship, nonprofit arts center The Church (48 Madison St., 631-919-5342) is the brainchild of local artists and residents Eric Fischl and April Gornick. Exhibitions at this haven for local writers, artists, musicians and dancers change often, while workshops, concerts, dances and performances offered during and in-between. Entry is open to the public and typically free.
Exclusively offering women-owned brands and products, Matriark (133 Main St., 631-919-5577) has everything from clothing and accessories to beauty products and furniture, and they donate $5 of each purchase to i-tri, an East End organization supporting the empowerment of adolescent girls through youth distance triathlon training.
Sylvester & Co. Modern General (103 Main St., 631-725-5012) gives HomeGoods a run for its money with an excellent selection of sundry gifts for the home and host. Need a little pick-me-up while out shopping? Sylvester’s own Dreamy Coffee cold brew is available at the shop’s café located inside.
Half a block away are Kites of the Harbor and the Wharf Shop (75 Main St., 631-725-9063; 69A Main St., 631-725-0420), two Main Street staples, with the latter being in business for over 50 years. Find ultra-unique toys, games, gag gifts, plenty of fun stuff for the kiddies and, you guessed it, kites.
Next door is Flashbacks (69 Main St., 631-808-3055), a clothing store with affordable basics. Everything from jackets, sunglasses, yoga pants, flowy maxi dresses and T-shirts are available. Need a quick yet thoughtful gift? Flashbacks also sells scented candles, great purses and bags, witty birthday cards, handmade soaps and just about every penny candy from your childhood.
Romany Kramoris Gallery (41 Main St., 631-725-2499) is another Main Street mainstay, and although it is in fact an art gallery, the myriad items for sale don’t necessarily have to hang on the wall. Antiques, beautifully bound journals, intricate ornaments and glassware, books, calendars, fragrances and ceramics are all sold here. Usually open ’til well after dark, it’s a perfect spot for perusing after dinner.
At the end of Main Street lies Sag Harbor’s Long Wharf. This is typically where the mega yachts park from Memorial Day to Labor Day and where locals and visitors alike can catch a killer sunset over the Sag Harbor Bridge. Hit up Ava’s & Around Again (1 Long Wharf St., 631-725-4067) in the Long Wharf Promenade where one goes for a dynamite thrifting experience.
New to the Sag Harbor scene is Kidd Squid Brewing Company (11 Spring St., 631-500-0533), a brewery inside the old train depot behind Main Street. Owners Rory McEvoy and Grainne Coen’s pink pastel-hued tasting room is perfect for a lounge and a pint. There’s also a beer garden created in conjunction with their neighbor, Sag Harbor Garden Center.
The swanky, historic American Hotel (45 Main St., 631-725-3535) has just under a dozen unique rooms, decked out in turn-of-the-century elegance. The Hotel (as it’s colloquially known) also houses a four-dining-room restaurant serving French-style cuisine and a wine list that’s a yearly recipient of Wine Spectator’s Award of Excellence.
Tucked away about two blocks from Main Street is Baron’s Cove (31 West Water St., 844-227-6672), a 60-plus rooms all-inclusive resort. The front-most building houses a cozy cocktail lounge, while the upstairs dining room serves waterfront-view breakfast, lunch and dinner.
Contemporary meets classic at Sage and Madison (31 Madison St., 631-530-0977) a boutique hotel located on the corner of Madison Street and Sage streets. Originally built in the late 1700s, guests enjoy Ralph Lauren bedding, Italian toiletries, Shifman luxury mattresses and other thoughtfully curated amenities. Located behind the main building in a small antique barn is Sage and Madison Boutique. Handmade jewelry, stylish home decor, and bath and body products are some of the goods located within. Coffee and tea are served at the boutique all day long.