Oyster Bay's annual Oyster Festival is held on the waterfront.

The hamlet of Oyster Bay, part of the greater Nassau County Town of Oyster Bay, is perhaps best known as the home of former U.S. President Theodore Roosevelt, whose regal Sagamore Hill estate still wows onlookers today. It’s a community steeped in colonial heritage and Gold Coast opulence, providing both tourists and locals alike with some of the finest waterfront access on the North Shore, along with a host of other natural, historic and manmade attractions.

Once Matinecock Indian land, English settlers first began purchasing parcels in Oyster Bay from the Matinecock in 1653, receiving an official charter from the crown for the township in 1667. Oyster Bay figured prominently in LI’s involvement in the American Revolution and like much of LI, blossomed in the 1800s once connected to the Long Island Rail Road (Oyster Bay welcomed its first LIRR train on June 21, 1889). Around this time, in 1880, Roosevelt had purchased 155 acres in Cove Neck, where his home was completed in 1885, when he was still a New York State Assemblyman.

“Filled with tree-lined streets, steeped in history from Colonial times straight through the Presidency of Teddy Roosevelt, as well as numerous amenities including parks, beaches, and facilities nationally recognized for their excellence, Oyster Bay has been consistently recognized as one of the best places to live in the nation by numerous publications,” said Oyster Bay Town Supervisor Joseph Saladino. “I encourage visitors to come and visit the town, as there is no place quite like it!”

These days, Oyster Bay is also famous for its annual Oyster Festival (theoysterfestival.org), one of the largest waterfront festivals on the East Coast, which draws some 200,000 attendees to the hamlet each year. The 35th installment of the festival happens this year on October 13 and 14 in Theodore Roosevelt Memorial Park and Beach (see below). Highlights include live entertainment, boats, artisans, pirate shows, rides and its famous oyster-eating and -shucking contest. There’s also a delectable food court, where scores of tempting oyster, clam and other seafood concoctions and traditional festival fare are served to hungry patrons.

But don’t let the Oyster Festival be the only reason you visit. Some recommended year-round Oyster Bay diversions include:

Long Island's Teddy Roosevelt
Long Island’s Teddy Roosevelt

HISTORICAL HAPPENINGS

One of the most iconic destinations in Oyster Bay, as well as the whole of Long Island, is Sagamore Hill National Historic Site (20 Sagamore Hill Rd., 516-922-4788, nps.gov/sahi), home of former President Theodore Roosevelt from 1885 until his death in 1919. Dubbed the “Summer White House,” this stunning 23-room Victorian mansion — preserved and still containing its T.R.-period contents — sits on an 80-acre estate that also contains a 37-acre National Environmental Study Area with forest, tidal salt marsh and bay beach areas. The site also holds the Theodore Roosevelt Museum, chronicling the life and career of the president, within the 1938 “Old Orchard” house used by Brigadier General Theodore Roosevelt Jr. (T.R.’s oldest son) and his family.

Another historic Oyster Bay Gold Coast estate that now delights the general public is Planting Fields Arboretum State Historic Park (1395 Planting Fields Rd., 516-922-9200, plantingfields.org), once the home of the W.R. Coe family, who enlisted the Olmsted Brothers to create a 400-acre arboretum renowned for its divine camellias, rhododendrons and azaleas. Attractions include the Main Greenhouse, which holds an extensive collection of hibiscus, orchids, succulents and seasonal displays as well as the impressive Coe Hall, formerly the Tudor Revival residence of the Coe family, which is open for guided tours from April to September, and features dazzling collections of furnishings, paintings, stained glass and decorative arts.

And to delve even further back into Oyster Bay history, stop in at the Raynham Hall Museum (20 West Main St., 516-922-6808, raynhamhallmuseum.org), ancestral home of the Townsend family, including Robert, who was a spy in George Washington’s Culper Ring during the American Revolution. The home was purchased by Robert’s father Samuel around 1740 and expanded, later being named Raynham Hall by Samuel’s grandson, Solomon, during a mid-19th century renovation. In the 1940s the front of the house was restored to its colonial appearance; today it boasts an exceptional collection of archives and artifacts of interest, including 5,000 items of furniture, works of art, household accessories, tableware, cookware, textiles, costumes, toys and games.

Street corner on the main drag in Oyster Bay. (Photo by MDLR MediaShutterstock)

ENGINE POWERED

In Oyster Bay, manmade creations of steel and machinery are revered alongside the hamlet’s historical and architectural leanings. Singer/pianist Billy Joel, a longtime Long Island resident and Oyster Bay denizen, transformed his phenomenal personal motorcycle collection into the museum 20th Century Cycles (101 Audrey Ave., 20thcenturycycles.com), where visitors can view 75-plus vintage bikes — some quite rare — all owned by Joel. The space is also used for the ongoing restoration and customization of some of the motorcycles. Who knows, you might even bump into the Piano Man himself.

Or, if four wheels are more your speed, there’s the Collector Car Showcase (85 Pine Hollow Rd., 516-802-5297, collectorcarshowcase.com), an automotive museum and sales showroom that specializes in more than 70 years of Porsche history. The museum also has a vintage BMW 507, Mercedes Benz 300SL, VW Bus and other rare non-Porsche vehicles also on display. There is also a complete car-care center located onsite, so you can get your oil changed or car detailed while you browse the free exhibits.

Train fans aren’t forgotten in Oyster Bay, either. For a comprehensive look at the history and importance of locomotive technology, and its impact on life on Long Island, spend some time at the Oyster Bay Railroad Museum (102 Audrey Ave., 516-558-7036, obrm.org), located near the historic Oyster Bay Railroad Station and Turntable, where a permanent museum will be opened in the future. The current interim center offers selected displays from the museum’s collection, exhibits outlining plans for the future museum, and a gift shop stocked with rail-themed goodies.

Coe Hall Historic house at the Planting Fields Arboretum (Photo by Joe TrentacostiShutterstock)

SIMPLE BEAUTY

With all those historic and motorized spots to visit, don’t forget to also amply enjoy Oyster Bay’s best natural feature: its waterfront. A great starting point in that spirit is The Waterfront Center (1 West End Ave., 516-922-7245, thewaterfrontcenter.org), which offers kayak, sailboat and stand-up paddle board rentals, pleasure cruises and a wide range of educational and junior programs, including sailing lessons for various levels of expertise.

You can also stroll along the Oyster Bay waterfront and maybe even catch a special event in Theodore Roosevelt Memorial Park and Beach (25 West End Ave., 516-624-6202), which is also the annual site of the Oyster Festival. The former marsh, once used as a dump and riddled with dilapidated shacks, was transformed into a popular public space in the late 1920s and donated to the town in 1942. It features walking paths, a marina, picnic areas, tennis courts, a softball field, children’s play area, and the Theodore Roosevelt Monument Assemblage, with 24 stones and a plaque that each tell a “chapter” in Roosevelt’s life story.

T.R.’s name also graces another of Oyster Bay’s natural treasures: the 15-acre Theodore Roosevelt Sanctuary and Audubon Center (134 Cove Rd., 516-922-3200, dec.ny.gov/outdoor/84505.html), which started out as the first Audubon songbird sanctuary in the nation. Today it offers a wide variety of activities, including environmental and conservation education, wildlife research, and more, while serving as home to 15 raptors, such as hawks, owls, falcons and a vulture, as well as reptiles and amphibians from around the globe. Explore the nature center and hiking trails, the latter of which are popular for birdwatching. An avid outdoorsman, T.R. would’ve likely given the sanctuary — and the greater Oyster Bay of today — an emphatic “bully.”

Oyster Fest is one of the biggest annual events on Long Island.

WHERE TO DINE

Wild Honey
1 E. Main St., 516-922-4690, wildhoneyrestaurant.com

Canterbury’s Oyster Bar & Grill
46 Audrey Ave., 516-922-3614, canterburysobg.com

Coach Grill & Tavern
22 Pine Hollow Rd., 516-624-0900, coachgrillandtavern.com

Taby’s Burger House
28 Audrey Ave., 516-624-7781, tabysburgerhouse.food93.com

Bonanza’s
25 Shore Ave., 516-922-7796, bonanzasitalianices.com

2 Spring
2 Spring St., 516-624-2411, 2springstreet.com

Sweet Tomato
91 Audrey Ave., 516-802-5353, mysweettomato.com

Autentico
124 South St., 516-922-2212, autenticooysterbay.com

The Homestead
107 South St., 516-922-9293, thehomesteadny.com

Pietro’s Brick Oven Pizza
342 Lexington Ave., 516-922-2023, pietrosbrickovenpizzaoysterbay.com

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Brendan Manley is an award-winning journalist, screenwriter and content development/marketing professional. He has extensive experience in newspaper and magazine publishing, as well as digital media, covering topics including arts and entertainment, sports, lifestyle, news, technology, travel and history. He is an ongoing contributor to Military History, Hotel News Now.com and HOTELS magazine, as well as the Long Island Press, where he formerly served as Managing Editor and Lifestyle section head. He is currently developing several of his original scripts for Hollywood, and consults on various film and scripted TV projects for studios, producers and financiers. Brendan is based in upstate New York's southern Adirondacks region.