Nestled among lush North Shore greenery and resting alongside the serene and scenic harbor that bears its name, the historic hamlet of Oyster Bay is among the most picturesque areas on all of Long Island. Whether you’re looking for a sunset walk along the shore, a peaceful hike through verdant trails, or a stroll over pristine park grounds, you can find it in this crown jewel of Nassau’s Gold Coast.
The area was first settled by the Dutch in the mid-17th century, and it was an important setting for the events of the American Revolution, but it wasn’t until then-president Theodore Roosevelt began spending his summers in nearby Sagamore Hill that Americans got to know just how stunning a place Oyster Bay really is.
If you come to the area in search of good food, unique shopping, gorgeous views, and fascinating history — or to enjoy the 40th annual Oyster Festival on Oct. 14-15 — you won’t be disappointed provided you stop by a few of the following spots:
THE BEST FOOD IN TOWN
The many menus of Oyster Bay offer something for every kind of palate. If you’re looking for a quick bite from a quaint café, an unforgettable fine dining experience, or anything in between, you’ll find it here. Here are just a few local favorite spots.
Sweet Tomato (91 Audrey Ave., 516-802-5353, sweettomato.business.site) is the perfect spot for a quick lunch stop. Their menu strikes a fantastic balance of fresh and light fare, like their salads and smoothies, and more indulgent and offbeat offerings, like their popular penne alla vodka chicken wrap.
Ranking pizzerias is a popular Long Island pastime. If you consider it one of yours, then be sure to try out Mama Mia’s Brick Oven Pizzeria (342 Lexington Ave., 516-922-2023, mamamiaspizzaria.com) when you’re in town to see how it stacks up against your all-time favorites. Try the sesame crust ricotta pie and odds are it’ll place high on that list.
Wild Honey (1 E Main St., 516-922-4690, wildhoneyrestaurant.com) is a popular lunch and dinner destination that offers inventive takes on familiar fare. Sure, you’ve tried calamari before, but have you tried Thai BBQ calamari? If not, you probably should.
For an intimate multi course dining experience with a carefully crafted menu, stop by 2 Spring (2 Spring St., 516-624-2411, 2springstreet.com). Along with their top flight brunch and dinner offerings, they’ve got an eclectic array of one-of-a-kind cocktails.
UNIQUE NORTH SHORE SHOPPING
These days it seems like you can get anything and everything by shopping online. But that’s not exactly true. You simply can’t replicate the experience of wandering through little boutiques and charming shops virtually—not yet, at least. Should you wander through some of these Oyster Bay shopping stops you’re bound to find something you didn’t even know you were looking for.
If you’re in the market for rare and beautiful additions to your wardrobe, you can’t do much better than Next To New Boutique (59 W. Main St., 516-922-3636) and chrison & bellina (24 Audrey Ave., 516-802-3824, chrisonbellina.com). You never know what you might find when visiting either of them, which is at least half the fun.
No fan of the written word can avoid the allure of a privately owned bookstore, nor should they. Theodore’s Books (17 Audrey Ave., 516-636-5550, theodoresbooks.com) is a newer addition to Oyster Bay’s charming small business selection. Much like a good book, it’s an easy place to get lost in, and a difficult one to leave.
Hive Market & Maker’s Space (102 Audrey Ave. Apartment 100, 516-588-9400, www.hivemarketob.com) offers a truly unique Oyster Bay shopping experience. There you’ll find a collection of one-of-a-kind artisanal items made by local creators, as well as a community-centric space where you can enjoy workshops, book clubs, classes, hosted events, and more.
THE ROOSEVELT EXPERIENCE
Easily the most famed champion of Oyster Bay’s rare beauty was former President Theodore Roosevelt, who spent summers at his home in Sagamore Hill during his time in office. Both Teddy and his wife, Edith, spent their twilight years in town and have been laid to rest at Youngs Memorial Cemetery in Oyster Bay Cove. Efforts to honor his contributions to the area have been pivotal in beautifying Oyster Bay and preserving its history.
There are many ways to appreciate President Roosevelt’s lasting impact on the area, including the following:
You can visit the Roosevelts’ Summer White House at the Sagamore Hill National Historic Site (20 Sagamore Hill Rd., 516-922-4788, nps.gov/sahi/index.htm) and share in the former president’s lifelong love of the natural world by hiking its beautiful grounds. Tours of the house are available by advanced reservation from Thursday to Sunday of each week.
The Theodore Roosevelt Sanctuary and Audubon Center (134 Cove Rd., 516-922-3200, ny.audubon.org/TRSAC) is a 14-acre expanse of preserved natural land that is home to an array of amazing wildlife as well as a number of picturesque hiking trails and gardens.
Overlooking the serene splendor of Oyster Bay Harbor is Theodore Roosevelt Memorial Park (63 Larrabee Ave., 516-624-6202), where you’ll find the Theodore Roosevelt Monument Assemblage: a series of memorial rocks which chronicle Roosevelt’s life in chapters. The park also offers hiking trails, a playground, picnic tables and benches, and of course, gorgeous waterfront views.
OYSTER BAY ARTS
Oyster Bay has all kinds of great destinations for art appreciators and aspiring artists alike. If you’re looking to take part in creative expression or simply observe it in action, check out some of these spots.
The vibrant poster art that came to represent both the psychedelic rock and counterculture movements of the 1960s has now become a form of fine art all its own. You can not only appreciate that art at The Bahr Gallery (95 Audrey Ave., 516-283-1967, bahrgallery.com) but you can even take it home with you. They have more than 200 rare and beautiful pieces of this fascinating period in American history on display, many of which are signed first printings.
Webbe and Webbe Fine Art (17 E. Main St., 516-674-4428, webbeandwebbefineart.com) represents a unique blend of fine art and family. There you’ll find the work of both photographer Deborah Webbe and her grandfather, painter and illustrator Frank Webbe. The art is beautiful, but the stories are what give it its true power.
When you’re looking to do some self-expression of your own, The Teaching Studios of Art (98 Audrey Ave., 516-558-7367, teachingstudios.com) is a fantastic place to start. They offer in-person and online art classes, as well as a variety of workshops that cover both the broader concepts of art and the finer points.
PLACES TO STAY IN OYSTER BAY
East Norwich Inn (6321 Northern Blvd., East Norwich, 516-922-1500, eastnorwichinnli.com)
The Inn at Fox Hollow (7755 Jericho Tpke., Woodbury, 516-224-8100, thefoxhollow.com/hotel)
The Mansion at Glen Cove (200 Dosoris Ln., Glen Cove, 646-518-8771, themansionatglencove.com)
PLACES TO EAT IN OYSTER BAY
Wild Honey (1 E. Main St., 516-922-4690, wildhoneyrestaurant.com)
2 Spring (2 Spring St., 516-624-2411, 2springstreet.com).
The Homestead (107 South St., 516-922-9293, thehomesteadny.com)
Café Al Dente (62 South St., 516-922-2999, cafealdenteoysterbay.com)