Bucket List: 15 Best Places to Visit in Oyster Bay, New York
Oyster Bay is a small, historical town on Long Island, New York, and serves as the vacation town of Theodore Roosevelt as he fulfilled his ambitions. His former residence is now a historic site that thousands of tourists visit. Oyster Bay is also home to several mansions and botanical gardens, including the Bailey Arboretum, a botanical garden with hundreds of different species of trees, shrubs, and exotic flowers. The first certified American Heart Association walking path is also in Oyster Bay, bringing visitors to 30 historic sites around the town.
Oyster Bay History Walk
Visitors can take a self-guided history tour of the village through the mile-long Oyster Bay History Walk. The self-guided walking tour leads to 30 historic sites in one loop. The Oyster Bay History Walk is the first certified American Heart Association Start! Walking Path on Long Island. The tour starts at Baykery Café with a general introduction to Oyster Bay and ends at Christ Episcopal Church, notable for holding President Theodore Roosevelt’s funeral service in 1919.
Oyster Bay Oyster Festival
The Oyster Bay Oyster Festival is an annual festival of the Oyster Bay Rotary Club run by the Oyster Bay Charitable Fund. The festival aims to promote the rich history and resources of Oyster Bay. It is the largest waterfront festival on East Coast, with more than 150,000 attendees each year. There are several entertainment activities at the festival, including live performances, pirate shows, and an oyster eating and shucking contest. The festival’s main highlight is the Food Court, where professional and volunteer chefs serve unique seafood dishes.
Location: 1 West End Avenue, Oyster Bay, NY 11771
Sagamore Hill National Historic Site
Sagamore Hill is the former residence of the 26th President of the United States, Theodore Roosevelt, from 1885 until his death in 1919. President Roosevelt’s legacy as a beloved leader and conservationist lasts to this day. During his presidency, Sagamore Hill served as President Roosevelt’s “Summer White House.” Several historical events took place on the Hill. The historic site is situated on 95 acres of land, including the 23-roomed Victorian-styled house outfitted as it was during President Roosevelt’s lifetime.
Location: 20 Sagamore Hill Road, Oyster Bay, NY 11771
Raynham Hall Museum
The Raynham Hall Museum is the home of the Townsend family, one of the founding families of Oyster Bay, and one of George Washington’s Culper Spy Ring agents, Robert Townsend. The museum has an extensive collection of 6,000 objects and artifacts on the Townsend family, Oyster Bay, and the greater Long Island area, including account books, ledgers, and photographs. One of the museum’s most important collections is the Townsend Family Papers containing the family’s manuscript letters, deeds, and business records, most especially Robert Townsend’s records.
Location: 30 W Main Street, Oyster Bay, NY 11771
Old Westbury Gardens
The Old Westbury Gardens is the former estate of John S. Phipps, his wife, Margarita Grace Phipps, and their four children. The Charles II-style mansion is surrounded by 200 acres of manicured gardens, woodlands, ponds, and a lake and is embellished with antique English furnishings. The star attraction of the property is the Walled Garden, designed by George Crawley and altered by Margarita Phipps. The Walled Garden has beds of delphinium, phlox and salvia, rose bushes, and tree peonies. Guided tours of the Old Westbury Gardens are offered, and events like horticultural demonstrations, workshops, botanical arts, and gardening classes are hosted on the property.
Location: 71 Old Westbury Road, Old Westbury, NY 11568
Planting Fields Arboretum State Historic Park
The Planting Fields Arboretum State Historic Park sits on the former Gold Coast estate of the W.R. Coe family. The park has 400 acres of woodlands, gardens, nature trails, and a large collection of orchids and succulents. The Camellia Greenhouse has the largest collection of camellias in the state. Visitors can get guided tours around the park and in the Coe Hall, the former Tudor Revival residence of the Coe family, where visitors can see the lavish lifestyle of the 1920s.
Location: 1395 Planting Fields Road, Oyster Bay, NY 11771
The Bailey Arboretum is the former estate of Frank and Marie Louise Bailey. The property ownership was transferred to Nassau County after Marie Louise Bailey passed away in 1968. It has been maintained and run by the Friends of Bailey Arboretum since 2006. The Bailey Arboretum is a 40-acre botanical garden with 600 different species of trees, rare shrubs, colorful flowers, and rock gardens. The garden had a recent addition, the Sensory Garden, specifically designed for the handicapped. The Sensory Garden is wheelchair accessible and has signs written in Braille.
Location: 194 Bayville Road, Locust Valley, NY 11560
The Muttontown Preserve is the largest preserve in Nassau County, with more than 500 acres of land to explore and hike. The landscape is relatively flat, with a few rolling hills and marked nature trails. The preserve is a favorite hiking spot with 20 miles of well– maintained hiking-only and multi-use trails. Birdwatching is another popular activity with ducks, waders, indigo buntings, and deep bluebirds around the preserve.
Location: 1861 Muttontown Road, Oyster Bay, NY 11545
Theodore Roosevelt Sanctuary and Audubon Center
The Theodore Roosevelt Sanctuary and Audubon Center is the nation’s first National Audubon Society songbird sanctuary, established in 1923. The 14-acre sanctuary has several ponds, hiking trails, native plant demonstration gardens, and the iconic Bessie Potter Vonnoh fountain sculpture. Twelve acres of the were donated in memory of President Theodore Roosevelt by his cousins W. Emlen and Christine Roosevelt. The Sanctuary has an array of outdoor and recreational activities, including hiking, birdwatching, and wildlife research. Some of the birds found in TRSAC are American Goldfinch, Ruby-throated Hummingbird, Common Grackle, and Hermit Thrush.
Location: 134 Cove Road, Oyster Bay, NY 11771
Bayville Adventure Park
Bayville Adventure Park is a nautical-themed adventure park in operation since 1859. The adventure park is a popular attraction for children, especially in the summer. The park has several attractions like Water Slides, Adventure Tower, Funhouse, Haunted House, Bumper Boats, Mini-golf, and Indoor Rock Climbing. The park has three on-site dining options: Beaches and Cream, Shipwreck Tavern, and Breakers Sports Bar and Grill.
Location: 8 Bayville Avenue, Oyster Bay, NY 11709
Big River Barn Rescue Inc.
Big River Barn Rescue Inc. is a horseback riding service specializing in riding on the trail. All of the horses rescued were abandoned, neglected, and abused, many of which were from racetracks. Big River Barn helps each horse recover from injuries and rehabilitate to a new life by giving them jobs by going out on trail rides. Big River Barn offers horseback riding and welcomes riders of all levels, including first-time riders.
Location: 1864 Muttontown Road, Oyster Bay, NY 11791
Oyster Bay Rail Road Museum
The Oyster Bay Railroad Museum is committed to showcasing Long Island’s railroad history and its impact on Long Island life. The museum collects and preserves each artifact and archive for future generations. Some of the retired coaches and caboose are the LIRR N52 Caboose #12, LIRR N52 Caboose #50, LIRR P54 Ping Pong Coach, and the LIRR BM-60 Baggage Mail Car #738, all of which have served the Long Island Rail Road.
Location: 1 Railroad Avenue, Oyster Bay, NY 11771
Town of Oyster Bay Ice Skating Center
The Town of Oyster Bay Ice Skating Center is a community skating rink with indoor and outdoor rinks. The Skating Center offers skating lessons, hockey lessons, and public skating sessions.
Location: 36 Audrey Avenue, Oyster Bay, NY 11771
Centre Island Beach
Centre Island Beach is a quiet and peaceful beach that stretches for 650 feet, allowing visitors to swim along Long Island Sound and Oyster Bay Harbor. Activities to enjoy along the beach are swimming, seashell collecting, and picnicking. This beach is a great place for combing since it’s relatively deserted.
Location: 36 Audrey Avenue, Oyster Bay, NY 11771
Dine around Oyster Bay
Oyster Bay has several bars, cafés, and restaurants that have been around for a long time and stay true to the rich nautical history of the gold coast. For an interesting beer experience, the Oyster Bay Brewing Company has daily taproom hours, serving craft beers since 2012. Some of the dining hotspots are Coach Meeting House and Wild Honey, while Sweet Tomato and The Homestead offer a more casual atmosphere. Bonanza’s Italian Ices has been serving Oyster Bay since 1889 with an extensive menu of ice flavors.
Address: 36 Audrey Ave Oyster Bay, NY 11771
How to get there
Oyster Bay can be accessed by car and train. Oyster Bay is the last stop on the Oyster Bay Line of the Long Island Rail Road. Private vehicles can take Exit 35N from the Northern State Parkway or Exit 40E from the Long Island Expressway.
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Oyster Bay NY Travel and Tour Packages
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