Since Covid, Sag Harbor (and the East End as a whole) saw a significant increase in the permanent population, creating alternate-season demand for businesses to remain open throughout the colder months. This new normal draws crowds to the old whaling village in numbers somewhere between the saturated summer months and Tumbleweed Tuesday, filling it with curious day-trippers, seasonal renters and year-round residents. While not exhaustive, consider this a family-friendly Sag Harbor guide for good food, unique shopping and creative entertainment all year long.
From huevos rancheros and pancakes, to burgers and vegan breakfast bowls, Estia’s Little Kitchen is a crowd-pleaser. The Mexican-American restaurant offers both breakfast and lunch six days a week, while dinner is served on Friday and Saturday. The aptly-named “Little Kitchen” fills up fast, so either come early or go late, as seats are limited and it’s first come first served. If you do get stuck waiting, be sure to grab a mimosa: Freshly squeezed OJ, super dry bubbles and served in a goblet. The best in town.
1651 Bridgehampton/Sag Harbor Tpke., 631-725-1045
Family owned and operated, the Cove Delicatessen sits just past Otter Pond on your way into town. For decades now, they’ve featured homemade German-style deli fare. Everything’s Boar’s Head, with a slew of specialty sandwiches available for both breakfast and lunch. Be sure to check out their recently added al pastor tacos (available from 11 a.m. to 2 p.m. only). Game changing.
283 Main St., 631-430-6708
At the fork between Main and Madison Streets is Il Capuccino restaurant. Classic Italian comfort-food dishes are found here. Crisp tablecloths and soft candlelight adorn the dark wooden dining rooms. Chianti bottles hang from the ceiling while Dean Martin plays in the background. It’s warm, it’s welcoming, it’s old school. Don’t refuse the breadbasket, for these house-made garlic knots are the star of the show.
30 Madison St., 631-725-2747
Page at 63 Main 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.
63 Main St., 631-725-1810
For a chic, half Manhattan-half Mediterranean vibe, head to Lulu Kitchen. Adjacent to the zig-zag bar is an open kitchen with a wood-fire grill at its center, where all the action is. Elevating the usual lunch and dinner suspects with their signature wood-fire twist on most dishes, the flame show doesn’t mean meat-only: Lulu also offers plenty of vegetarian apps and entrees. The faint yet pleasantly constant murmur around the room adds an extra dose of conviviality to this eatery, open for dinner Wednesday through Monday.
126 Main St., 631-725-0900
Back in 2019, K Pasa opened in the same space where La Superica lived for decades at the foot of the bridge across from Long Wharf, aiding locals at a loss for affordable fare. K Pasa delivers solid Mexican fare and killer margaritas to fill the space left by Supe’s absence, offering specialty tacos for $6 each. The taqueria-inspired restaurant does it tapas style, also serving salads, rice bowls, chips and dips, birria and ceviche. Breakfast is offered every morning starting at 9 a.m. and brunch is weekends from 9 a.m. until 3 p.m. The spicy snap of their margarita is delightful, made with jalapeño-infused tequila and a homemade togarashi rim. Pair that with a cheeseburger empanada and peruse their ample list of sustainable tequilas, mezcals, beer and wine.
2 Main St.
Famed chef and restaurateur Laurent Tourondel’s LT Burger may be gone, but his second Sag Harbor enterprise, Sag Pizza, serves burrata, seared octopus, handmade pastas and gelato at this bright, cheerful staple. It’s their crispy Neapolitan-style personal pizzas that make them special, cooked in a wood-fire oven and featuring fresh ingredients with a near perfect ratio of sauce and cheese. There’s a “bambini” section available for the kids and just about every San Pellegrino soft drink available under the sun. For a couple extra bucks, be sure to indulge in a few house-made crust dippers, arguably the best part of the Sag Pizza experience. Bonus: Guests can test their pizza-making chops with a take-home dough kit.
103 Main St., 631-725-3167
Smack dab in the middle of town is Sag Harbor Cinema. It’s easy to spot, illuminated by the restored, iconic neon red “Sag Harbor” sign on the front of the building. New blockbuster releases to old Hollywood classics and independent documentaries grace the cinema’s silver screen. Movies are typically shown every day and ticketholders can pop upstairs to the theater’s Green Room, a lively rooftop bar and outdoor deck.
90 Main St., 631-725-0010
For over 30 years now, Bay Street Theater 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, and classes in acting, improv and voiceover in the upcoming weeks.
1 Bay St., 631-725-9500
Just up the street from Il Capuccino is The Church. Formerly a Methodist house of worship, this nonprofit arts center is the brainchild of local artists and residents Eric Fischl and April Gornick. Open for two years now, The Church is considered a haven for local writers, artists, musicians and dancers. Exhibitions change often, with workshops, concerts, dances and performances offered during and in-between. Entry is open to the public and typically free.
48 Madison St., 631-919-5342
Set back atop a hill inside one of the village’s old Victorian homes is Matriark. Exclusively offering women-owned brands and products, Matriark has everything from clothing and accessories to beauty products and furniture. Ever philanthropic, the folks at Matriark pledge to donate $5 of each purchase to i-tri, an East End organization set for the empowerment of adolescent girls through youth distance triathlon training.
133 Main St., 631-919-5577
Sylvester & Co. Modern General gives Home Goods a run for its money. Books, cookware, beauty products, candles, clothes; these are just some of the offerings inside the Sag Harbor locale. Need a little pick-me-up while out shopping? Sylvester’s own Dreamy Coffee brewed, cold brew and beans (they also just did a delicious stout collaboration with local Spring Street brewer, Kidd Squid Brewing) are available at the shop’s café located inside, along with a few restorative sweet treats. The price is dreamy too, with a small cup costing a dollar during the week.
103 Main St., 631-725-5012
Half a block away are Kites of the Harbor and the Wharf Shop, 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.
75 Main St., 631-725-9063; 69A Main St., 631-725-0420
Next door is Flashbacks, a clothing store that offers cute and 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, incense and just about every penny candy from your childhood you can think of.
69 Main St., 631-808-3055
Romany Kramoris Gallery 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.
41 Main St., 631-725-2499
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. Newly renovated a couple of years ago, the Wharf now includes an extended wrap-around walkway for pedestrians. Ava’s & Around Again in the Long Wharf Promenade is where one goes for a dynamite thrifting experience. Designer items can be found for a fraction of the original price.
1 Long Wharf St., 631-725-4067
Step back in time at the swanky American Hotel. This historic gem has under a dozen rooms, all equally unique and equally decked out with timeless luxuries. Visitors can enjoy turn of the century elegance in both their room and at dinner, as the Hotel (as it’s colloquially known) also houses a four-dining room restaurant. French-style cuisine is served for breakfast, lunch and dinner 365 days a year. The locale’s wine list is a yearly recipient of Wine Spectator’s Award of Excellence. If slurping down a dozen local oysters, sipping a glass of Billecart brut and sleeping on Frette linen is for you, then look no further.
45 Main St., 631-725-3535
Tucked away about two blocks from Main Street, travelers can lay their heads at Baron’s Cove. Within the past 10 years, New York-based real estate developers Cape Advisors renovated the grounds, refurbishing the former motel’s 60-plus rooms and transforming it into the all-inclusive resort of the village. The front-most building at Baron’s houses a cocktail lounge with a roaring fireplace and cozy seating. The upstairs dining room serves breakfast, lunch and dinner, with waterfront views and fresh takes on classic dishes. Baron’s is currently closed for their “winter refresh,” but is slated to reopen February 10.
31 West Water St., 844-227-6672
Contemporary meets classic at Sage and Madison, Sag Harbor’s new boutique hotel located on the corner of Madison Street and Sage Street. Open since 2020, there are two suites and a one bedroom available for lodgers at the historic site, originally built in the late 1700s. Guests can enjoy Ralph Lauren bedding, Italian toiletries, Shifman luxury mattresses and other thoughtfully curated amenities. The “Hall” and “Hatfield” suites contain two bedrooms each, while the “Madison” is a smaller one bedroom. Located behind the main building in a small antique barn is Sage and Madison Boutique. Handmade jewelry, stylish home decor, home and garden accessories and bath and body products are some of the goods located within. Coffee and tea are served at the boutique all day long.
31 Madison St., 631-530-0977