Blake Walsh

15 Best Things to Do in Oyster Bay, NY

  • Published 2023/04/09

Oyster Bay is a little historic town and the easternmost of the three towns that make up Nassau County, New York.

It is part of the metropolitan area of New York with 20 incorporated villages and 17 unincorporated hamlets.

Likewise, it is the only town to stretch from the north to the south shores of Long Island.

Oyster Bay is made famous for the legacy US President Theodore Roosevelt left behind.

See his historic residence and summer White House in the village of Cove Neck, which has been restored and is now a museum.

Besides Roosevelt’s legacy, there are more reasons to visit this town as part of Long Island’s famous Gold Coast.

Oyster Bay makes an ideal escape from the bustling city for its quaint and charming art, history, and nature.

Here are the best things to do in Oyster Bay, New York.

Visit the Sagamore Hill National Historic Site

House at the Sagamore Hill National Historic Site

littlenySTOCK /

A Victorian Mansion built in 1885, Sagamore Hill is now the Sagamore Hill National Historic Site.

It was the residence of Theodore Roosevelt until his passing in 1919.

From 1902 through 1908, it also functioned as the “Summer White House” of the 26th President, where Roosevelt hosted prominent figures from around the nation and the world.

Furnished in shingle style, this historic site features memorabilia from the President’s life, trophies from his “big game” expeditions, and gifts from foreign leaders.

Welcome sign of the Sagamore Hill National Historic Site

Felix Lipov /

The Sagamore Hill National Historic Site includes the Theodore Roosevelt Museum at Old Orchard.

It features more Roosevelt memorabilia, such as film footage with a remarkable narrative presentation.

The Sagamore Hill National Historic Site is owned and run by the National Park Service.

History board at the Sagamore Hill National Historic Site

littlenySTOCK /

Hang Out at the Theodore Roosevelt Memorial Park

Marker of Theodore Roosevelt Memorial Park

Idoysterbay, CC BY 3.0, via Wikimedia Commons

Theodore Roosevelt Memorial Park is a waterfront park in Oyster Bay’s hamlet commemorating US President Theodore Roosevelt.

The park’s west side contains a softball field, basketball and tennis courts, and a children’s play area.

The east side has circulating walkways arranged in a geometric pattern that leads from the park entrance towards the water to the north, where a giant flagpole stands in the plaza.

This side to its west is called “Zone B” and is used more for quiet recreation and memorial purposes.

Some of the memorials at the park are a stone with a plaque in honor of Roosevelt located at the entrance and a Theodore Roosevelt Monument Assemblage.

It includes artifacts and 24 stones representing significant chapters of Roosevelt’s life.

Theodore Roosevelt Memorial Park also features a pavilion, a beach for swimming and other water activities, and boat launch ramps.

Catch Fish at Oyster Bay Mill Pond

Oyster Bay Mill Pond is one of Nassau County’s few freshwater fishing locations accessible to the public.

Situated on a United States Fish and Wildlife Preserve, Oyster Bay Mill Pond spans 40 acres with a maximum depth of five feet and a shoreline of 1.43 miles.

Oyster Bay Mill Pond is famous for its brown and rainbow trout stocked every spring and fall season.

The pond also contains natural reproducing fish species such as largemouth bass, carp, chain pickerel, brown bullhead, and American eel.

Another popular fishing location to consider is Massapequa Lake, located at the southern end of the Town of Oyster Bay.

See Railroad Artifacts at the Oyster Bay Railroad Museum

Exterior of the Oyster Bay Railroad Museum

Antony-22, CC BY-SA 4.0, via Wikimedia Commons

The Oyster Bay Railroad Museum is located in the scenic hamlet of Oyster Bay.

It preserves Long Island’s rich railroad history and legacy.

The Railroad Museum has made considerable efforts in obtaining the funding necessary to restore the historic Oyster Bay Railroad Station and Turntable.

The restoration includes acquiring additional pieces of classic railroading equipment.

In February 2008, the Oyster Bay Railroad Museum’s Visitor Center finally opened.

The preview center displays railroad memorabilia and interactive exhibits, plan projections, and a museum store, while the display yard has a full-size railroad rolling stock and other equipment.

TheOyster Bay Railroad Museum is run by the non-profit group Oyster Bay Railroad Museum.

Immerse in Nature at the Planting Fields Arboretum State Historic Park

The grounds of Planting Fields Arboretum State Historic Park

Joe Trentacosti /

The Planting Fields Arboretum State Historical Park is a lively and vibrant location.

It is home to several historic structures, horticultural collections, world-class art, and Olmsted Brothers-designed gardens.

Formerly a Gold Coast estate, it still stands today as a tribute to art, culture, history, and people who had lived there.

The name “Planting Fields” referred to the land’s fertility and rich agricultural value for the Matinecock People, the English, and Dutch colonists.

Main house at Planting Fields Arboretum State Historic Park

Jaclyn Vernace /

Today, Planting Fields Arboretum State Historical Park welcomes more than 200,000 visitors annually.

It holds several iconic cultural events and festivities, including the Camellia Festival, Arbor Day, Home for the Holidays, concerts, lectures, exhibits, races, family events, and more!

The 1952-founded Planting Fields Foundation manages the 409 acres of this 20th-century estate in cooperation with the New York State Office of Parks, Recreation, and Historic Preservation.

Vibrant blossoming tree at Planting Fields Arboretum State Historic Park

Felix Lipov /

Learn to Sail with the WaterFront Center

The WaterFront Center (WFC) is a non-profit organization to inspire people of all ages about marine life and its environment.

The WaterFront Center’s mission is to “Connect People To The Water Through Education and Recreation” and encourage them to enjoy and protect it for a lifetime.

The Oyster Bay Sailing School works with the CHRISTEEN, the oldest oyster sloop in the country and a National Historic Landmark.

They provide educational opportunities, certification courses, sunset sails, boat and kayak rentals, and more.

Learn how to sail, rent a kayak or a sailboat, and join sailboat racing.

You will also learn to organize a private charter, take swimming lessons, send your children to summer camp, go fishing with the pros, and more.

The Waterfront Center looks forward to your visit to Oyster Bay Harbor, the gorgeous harbor on the Gold Coast!

Spot Birds at Theodore Roosevelt Sanctuary and Audubon Center

A water fountain at Theodore Roosevelt Sanctuary and Audubon Center

Kenneth C. Zirkel, CC BY-SA 4.0, via Wikimedia Commons

Audubon New York runs the Theodore Roosevelt Sanctuary and Audubon Center.

It was the country’s first National Audubon Society songbird sanctuary in 1923.

At the end of the sanctuary property is the Youngs Memorial Cemetery, where President Theodore Roosevelt was buried.

The sanctuary boasts 14 acres of vast native plant demonstration gardens, a mile of hiking trails, a few small ponds, and the famous fountain sculpture by Bessie Potter Vonnoh.

Signage of Theodore Roosevelt Sanctuary and Audubon Center

Kenneth C. Zirkel, CC BY-SA 4.0, via Wikimedia Commons

The Theodore Roosevelt Sanctuary and Audubon Center is a dynamic resource offering various programs, including wildlife research, environmental education, and conservation campaigns.

The sanctuary has 15 non-releasable raptors, including falcons, hawks, owls, and a vulture.

Also, visitors can get to know the local reptiles and amphibians worldwide.

A birdhouse at Theodore Roosevelt Sanctuary and Audubon Center

Kenneth C. Zirkel, CC BY-SA 4.0, via Wikimedia Commons

Take a Hike at the Muttontown Preserve

Chelsea mansion at Muttontown Preserve

DanTD, CC BY-SA 4.0, via Wikimedia Commons

The Muttontown Preserve is the biggest nature preserve in Nassau County.

It has roughly 550 acres of woodlands, fields, estate rounds, and ponds formed by the combination of three old estates.

Miles of marked trails within the preserve are home to the region’s trees, wildflowers, mammals, birds, amphibians, and reptiles.

Within the Preserve is the 40-room Chelsea Mansion, built in 1929 and included on the National Register of Historic Places.

It showcases Long Island Gold Coast Era’s architectural design with Chinese, English, and French influences.

The 60-room mansion of King Zog’s Knollwood Estate was built on this property but was demolished in 1959.

However, some remnants still exist in broken steps and fountains.

The Nassau Hall, another Gold Coast estate constructed in 1903, is also a part of the Preserve.

The Nassau County Department of Parks, Recreation, and Museums owns and operates the Muttontown Preserve.

With miles of designated nature trails, enjoy a self-guided tour or join one of their guided tours or educational programs.

Experience History at the Raynham Hall Museum

Exterior of the Raynham Hall Museum

Idoysterbay, CC BY 3.0, via Wikimedia Commons

The Raynham Hall Museum was the residence of the Townsend family, one of Oyster Bay’s founding families.

Robert Townsend was also an agent of the Culper spy ring organized by General George Washington during the Revolutionary War.

The Town of Oyster Bay now owns the house, and the Friends of Raynham Hall Museum, Inc. operates the property as a public museum.

The Raynham Hall Museum grounds span two-thirds of an acre, forming a sanctuary of beauty in the center of the village of Oyster Bay.

The lovely gardens were designed to coincide with two different eras represented by the house.

The Colonial garden features brick pathways bordered by ferns and daylilies, boxwood hedges, and French lilac ornamental elements.

In contrast, the Victorian garden features serpentine ivy beds mixed with rhododendrons, white pine trees, and mountain laurels.

The Raynham Hall Museum is said to be haunted, with recorded accounts of ghost sightings and sounds dating back to the early 20th century.

Raynham Hall is in the National Register of Historic Places, a designated Town of Oyster Bay Landmark, and a featured stop on the Oyster Bay History Walk audio walking tour.

Other Things to Do Nearby

Stop by the Hicksville Gregory Museum

Exterior of the Hicksville Gregory Museum

Muncharelli, CC BY-SA 3.0, via Wikimedia Commons

The Hicksville Gregory Museum, housed in the 1895 Heitz Place Courthouse, exhibits the largest public collection of minerals, butterflies, and fossils on Long Island.

Also, the museum features artifacts and photographs documenting the growth of Hicksville and the surrounding community.

Permanent fossil displays include mosasaur and dinosaur bones, dinosaur eggs (one with its embryonic bones revealed), adult and young Platybelodon fossils, trilobites, ammonites, petrified wood, and more.

The Hicksville Gregory Museum offers tours and learning programs on moths and butterflies, earth sciences, and paleontology by appointment.

In 1974, the United States Department of the Interior designated the structure as a National Historic Place.

This museum is in Hicksville, New York, 15 minutes from Oyster Bay.

Walk the Gardens of the Bailey Arboretum

The Bailey Arboretum is a stunning 42-acre arboretum in the hamlet of Locust Valley and home to the world’s largest Dawn Redwood (Metasequoia).

It is located on the property of famous philanthropist and horticulturist Frank Bailey.

It is a living museum promoting connections between humans and the natural world.

The Bailey Arboretum engages the community through engaging educational programs and both private and public events.

The Dawn Redwoods, located throughout the property, are among its most well-known specimen trees.

The mature trees have a “ropy” trunk and a pointy silhouette.

They are lovely in all four seasons, as the new green leaves in the spring turn golden before the needles fall off.

Bring the entire family so they may explore the well-marked trailways, serene gardens, and the freedom to wander the gorgeous grounds!

This place is in Locust Valley, New York, nine minutes from Oyster Bay.

Play a Round of Golf at Pine Hollow Club

Pine Hollow Club is a private golf club in East Norwich, New York, seven minutes from Oyster Bay.

It offers its members a top-notch country club experience.

Their magnificent 18-hole Championship course is one of the best-ranking golf courses in Long Island.

It has picturesque rolling hills, fairways that wind through the park-like landscape, and strategically positioned bunkers.

Tennis members can enjoy their six Har-Tru Championship courts, Long Island’s first Padel court, and three Pickleball courts.

They have seating for spectators and are surrounded by colorful gardens and lovely rolling hills.

The club was once the Long Island vacation home of Dorothy Schiff, the owner of the New York Post.

Then, it became the Gold Coast Mansion of Consuelo Vanderbilt and became the venue of the first PGA event in Long Island.

Pine Hollow Club pays homage to the club’s historical legacy while integrating today’s modern conveniences.

Go Rock Climbing at Island Rock

Island Rock is the longest-running indoor climbing facility in Long Island, committed to serving the climbing community in the area!

Island Rock opened in 1996 as a cutting-edge indoor rock climbing center constructed by RockWerx and Solid Rock Wall Systems.

Island Rock features a distinct and seamless climbing surface resembling a natural indoor rock!

They provide climbing for people of all ages and skill levels and have walls designed for beginners who want to rediscover their love of climbing trees.

Experts who climb recreationally and compete all across the country and the world are also welcome there.

Challenge yourself on more than 14,000 square feet of climbing space, 30-foot climbing walls, and up to 15-foot boulders.

It also has two crack climbs, over 100 top rope routes and boulder problems, cardio and strength training equipment, a yoga room, and much more!

Island Rock is in Plainview, New York, 16 minutes from Oyster Bay.

Meditate at the John P. Humes Japanese Stroll Garden

The John P. Humes Japanese Stroll Garden is a unique and historically significant seven-acre landscape in Mill Neck, New York, six minutes from Oyster Bay.

It houses a remarkable variety of Asian and North American plants, creating a lovely Japanese scene and stimulating a meditative experience.

This unique garden was created by Ambassador John Portner Humes and his wife after a trip to Japan in 1960.

Heavily influenced by their trip, Ambassador Humes brought the Tea House still in the garden.

He contracted landscape designers Douglas and Joan DeFay to create the park on their Mill Neck estate.

The DeFays created a world-class Japanese walking garden on two acres of rolling woodlands on Long Island’s North Shore over the next four years.

More elements were added in the following years, including a new entranceway adorned with Japanese maples and native woodland wildflowers, bamboo groves, a wisteria arbor, and a rocky shoreline.

The garden first opened to the public in 1986.

However, after a few years of operation, it became clear that the garden needed more funding to ensure its future.

The Garden Conservancy took over stewardship of the garden in 1993.

For preservation purposes, the North Shore Land Alliance acquired the John P. Humes Japanese Stroll Garden in 2017.

Bring the Family to Bounce! Family Entertainment Center

Bounce! Family Entertainment Center is a terrific indoor recreation facility fit for people of all ages!

Everyone will delight in their many attractions, including Bumper Cars, Laser Tag, Slam Dunk Basketball, Trampoline Dodgeball, Rock Climbing, Axe Throwing, Soft Play Arena, Ninja Course, and so much more.

Toddlers can also share the fun at Toddler Town, so no one gets left out!

Bounce! Family Entertainment Center also provides a location for private gatherings like birthday celebrations.

Bounce! Bites, the facility’s in-house kitchen and snack bar, serves delectable appetizers and snacks, perfect for snacking between family activities.

This entertainment center is in Syosset, New York, 12 minutes from Oyster Bay.

Final Thoughts

Oyster Bay is a paradise for history, nature, and recreation seekers, thanks to its stunning beaches, historic landmarks, lush gardens and parks, and picturesque scenery.

Whether you stay for a day or two or spend a whole week of exploration, visitors will feel there’s so much to uncover!

Discover the best things to do in Oyster Bay, New York!

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