Fun & Unique Things to Do in Oyster Bay, Long Island 

A woman in Roosevelt's House in Oyster Bay, Long Island

Oyster Bay is one of the best towns on Long Island to visit for history, outdoors, and food. There’s a reason it’s called Oyster Bay–the water and swampy areas are teaming with oysters at every turn! One of this small ocean town’s most famous residents was former President Theodore Roosevelt, who took an active hand in conversation efforts in the area. Many of the fun things to do in Oyster Bay revolve around his summer home, property, and the national parks he was passionate about protecting. An equal balance between indoor and outdoor entertainment and a mix of ocean and wilderness makes Oyster Bay one of the best charming small towns to visit on Long Island–there is always something to do!

How to Get to Oyster Bay

  • Train: LIRR goes direct from Jamaica for $7.75 (off-peak)
  • Driving: But there is a ton of traffic there, so I recommend taking the LIRR
  • Uber: Uber costs about $100 from Brooklyn to Oyster Bay. But I recommend doing LIRR to avoid traffic. And then you can order an Uber when in town. While the downtown is very walkable and has a lot of cute things to see and do, to get around other cool parts (like Sagamore Hill), it costs about $8 to each place. Not bad!

Things to Do in Oyster Bay, Long Island

1. Sagamore Hill National Historic Site + Theodore Roosevelt’s Home & Eel Creek ★

Sagamore Hill National Historic Site is located in Cove Neck near Oyster Bay on the North Shore of Long Island. The property contains the former home of Theodore Roosevelt and many other historic sites open for touring.

Also called the Summer White House, the Theodore Roosevelt Home Museum is the former summer home of the 26th president, where he lived from 1885 to 1919 until his passing. The Queen-Anny style residence has 23 rooms to explore, with mostly original fixtures and decor used by the Roosevelt family! You can only gain access to the house by booking a tour, lasting about 45 minutes each, and offered on a Thursday through Sunday schedule. The museum is located on Sagamore Hill Historic Site, and tours provide illustrated stories about the home and outdoor grounds. 

Theodore Roosevelt loved the outdoors and conserving natural wonders. In return, there are tons of trails around the property to explore the protected woods, fields, salt marshes, and beaches that so many local species call home. 

One of the trails leads to Eel Creek and Cold Spring Harbor, featuring scenic waters and opportunities to view wildlife. You MUST stay on the path here, and it’s advised to check for seasonal flooding before your visit, as the high tide can flood the paths leading to the boardwalk. The site is open from sunrise to 30 minutes after sunset. There are no tickets available for purchase onsite, and all must be booked on

  • Hours: Thursday afternoons to Sunday 
  • Cost: $10 for a touru

2. Planting Fields Arboretum & State Park ★

Planting Fields Arboretum is another former estate turned into a historic state park with spectacular gardens. There are over 409 acres of rolling hills, flower collections, fountains, greenhouses, and woodland paths. Inside the 65-room Tutor revival estate, visitors can book a guided tour or take a self-guided tour through Coe Hall. The home is full of artistry and craftsmanship, from the custom ironwork to the murals painted by artists Everett Shinn and Robert Winthrop Chanler. You can also participate in events at the arboretum, including the Spring 5K, flower festivals, pride celebrations, and more. 

  • Hours: 9:00 am to 5:00 pm 
  • Cost: Parking fee is $8 per car; tour fees range from $5-$10, with kids under 6 free

3. Dinner & Drinks at 2 Spring ★

2 Spring is a contemporary American restaurant with a beautiful ambiance and tons of natural light shooting through walls and ceiling windows. They specialize in serving European-style multi-course meals to small groups. We tried a few other places in the area, and this was by far the best for intimate cocktails; very relaxing. The restaurant is open for dinner (Tuesday to Sunday) and brunch (Saturday and Sunday), with some very unique choices on the menu, especially under the light & raw bar.  

4. Oyster Bay Brewing Company

Oyster Bay Brewing Company is one of our favorite breweries in Nassau County, staying true to their nautical roots and native locals. They’re the creators of Barn Rocker–the official beer of the NY Islanders–and offer more than 15 craft beers on tap. You can order a large tasty pretzel at the bar or bring in your own food from home or a local eatery. The taproom is located just minutes from the Gold Coast, making this one of the best breweries on Long Island to stop at while you explore the seaside of Oyster Bay. 

5. Theodore Roosevelt Sanctuary & Audubon Center

This sanctuary, nestled into Oyster Bay Cove Village, was the first songbird sanctuary in the country! Theodore Roosevelt’s involvement in conservationism who one of his most significant accomplishments and contributions to his country. He established more than 51 bird reserves, 150 national forests, 4 game preserves, five national parks, and more!

In line with his love for nature, the Theodore Roosevelt Sanctuary has many activities for visitors, including viewing 15 types of non-releasable raptor birds: owls, hawks, vultures, and falcons. Other wildlife you can see are amphibians and reptiles local to New York and from around the world. There are hiking trails, gardens, and a Nature Center on the property, spreading over 15 acres, right down the road from Sagamore Hill and The Roosevelt Home. 

6. Cooper Bluff Waterfront Bar

Cooper Bluff Waterfront Bar is the ONLY waterfront bar in Oyster Bar, with a nice outdoor space. It’s kind of a younger, college-age crowd at night, and it can be hard to get a seat after a certain time. They have a food truck with finger foods and sometimes have live music.  It’s about a 20-minute walk from the Oyster Bay train station. Once you get there, you have to walk on pebbles and rocks, so wear comfortable shoes. It gets cold after the sunset, so bring a warm sweater. We didn’t really like how loud and crowded it was and left soon after. If you want something quieter, 2 Spring is much better.

7. 20th Century Cycles

Famous singer-songwriter and pianist has called Oyster Bay, Long Island home for over 20 years, and his love for motorcycles lives at 20th Centruy Cycles! This shop was created specifically to host, service and maintain Joel’s expansive collection of vintage motorcycles. Visitors can view over 75+ bikes and tour the shop to see how these metal machines are kept so immaculate. The shop is open to the public Saturdays and Sundays with free admission!

8. Raynham Hall Museum 

This small museum in Oyster Bay was once home to the Townsend family and Robert Townsend, George Washington’s intelligence operative! Raynham Hall Museum is built in a 300-year-old home, giving visitors a glimpse into what it was like to live on Long Island in the 18th and 19th centuries. The building was renovated back in the 1940’s to return the home to its original Colonial aesthetic and hosts several exhibits teaching guests about what it was like to be a heroic patriot and live the life of espionage in Washington’s ring of spies. The Historic Spirits Tour is offered all year round, with an opportunity to explore the property alongside a Spiritualist Healer. 

9. Go Shopping 

  • Theodore’s Books: This indie bookshop is nestled into the historic district of Oyster Bay town and is a favorite activity for literary visitors. Theodore’s Books was started by owner Steve Israel, book lover and former congressman, who named the shop after the beloved Theodore Roosevelt. It began as a project to put politics aside and embrace the youthful sense of adventure Roosevelt brought to the area. They have over 10,000 titles for readers of all ages, and the staff is incredibly helpful. 
  • Hope Thrift Shop: Hope Thrift is located on Audrey Ave and is perfect for shoppers looking for second-hand treasures. They highlight weekly items on their Facebook page, and all profits go to the Benevolent Fund, an organization serving youth ministries,  single mothers, and outreach programs. 
  • Hive Market and Maker’s Space: If you want Ocean Bay activities that support local artisans, you can shop for one-of-a-kind products at Hive Market and Maker’s Space. They serve as a shared workspace for artists and craftsmen to create together and provide a brick-and-mortar shop to sell their creations. 
  • The Bahr Gallery: Art lovers can shop for some stunning finds at the Bahr Gallery, showing off psychedelic posters from the 1960s. The posters feature creations by Stanley Mouse, Victor Moscoso, Rick Griffin, and more from the era of the Summer of Love. The gallery is only open from Thursday to Saturday. 

10. The Waterfront Center ★

It’s hard to visit Oyster Bay and not want to get out on the water with all the scenic views. The Waterfront Center is a non-profit organization that helps visitors explore the Long Island waters through the Long Island Sound and Oyster Bay Harbor. They provide a variety of marine educational programs for those looking to learn and grow their boating skills, as well as rentals and tours on CHRISTEEN, the historic oyster sloop. 

  • Sailing: The center has sailing classes available to all ages and ability levels, from beginner to expert. They are a U.S. Sailing Accredited School and Sailing Center and offer lessons starting from exploring the water on a sailboat to learning to sail to certification courses. If you know how to sail and just need a rental, you can book a boat starting May 1. 
  • Kayaking: Kayak rentals start on Memorial Day to Columbus Day weekend with choices for single and double kayaks or stand-up paddleboards. Trips explore the National Wildlife Refuge on the protected waters of the Long Island Sound and Oyster Bay Harbor, making it one of the best places to go kayaking on Long Island if you also want to swim! If you have a big group, try renting the new giant 17ft paddle board that hold six people!

11. Go Hiking 

Oyster Bay is close to some of the coolest hiking trails on Long Island, some leading you right along the water. Most of these do not allow pets so best to leave the pups at home. 

  • Bailey Arboretum: Only a 10-minute drive from Oyster Bay, the trails in Bailey Arboretum are easy, marked woodland paths with three different routes: Wide Loop, Evergreen Arbor, and Great Law Trail. The arboretum has 42 acres of land, an Upper and Lower pond, and peaceful gardens, and is open all year round. They also have the World’s Largest Dawn Redwood, so don’t forget to check that out! 
  • Muttontown Preserve: Muttontown Preserve is Nassau County’s largest nature preserve, with 550 acres of woodlands, fields, and ponds on old estate land. There are miles of marked nature trails on the preserve exploring the local vegetation, wildflowers, and many species of birds, amphibians, reptiles, and mammals. The main loop is about 2.5 miles and is considered easy. Trails are open year-round and popular for cross-country skiing in the winter. 
  • Shu Swamp: This is another easy hike located in the North Shore Wildlife Sanctuary with two different loops: Blue and Red. Both trails start on the Red Loop, which then continues on around the pond area. The Blue Loop leading to Humes Preserve has unimpressive views of the residential areas and roads towards the middle of the hike that may not be worth the time. 
  • Tiffany Creek Preserve: This easy loop is located right in Oyster Bay, spanning about 2.8 miles through old-growth oak forests. The trail is perfect for hiking, birding, and running. While easy in ability, it can become a little rugged with uneven surfaces and rocky areas, and some parts are poorly marked. The entrance to the trails is at Sandy Hill Rd and Berry Hill Rd.  

12. Humes Japanese Stroll Garden 

These gardens are one of the most unique things to do in Oyster Bay, only 7 minutes from the historic district. The Humes Japanese Stroll Garden is a mix of Japanese and North American wilderness, designed as a meditative experience inspired by the mountains and the sea. Most of the garden is easy to navigate aside from a gentle stone climb. It’s easy and takes you to a ‘mountain peak’ with a gravel path stream leading to a beautiful Japanese tea house by the pond. The gardens are open end of April to the end of October. 

13. Oyster Bay Rail Road Museum 

You really learn to appreciate the role of the railroads running through Long Island when you visit the Oyster Bay Rail Road Museum. This attraction is small but packed with history, open for visitors from April to early November. The Oyster Bay Rail Road station was first constructed in 1889 by the Long Island Rail Road before it was turned into a New York State Landmark in 2004. Currently, the museum is set in the Visitor Center in downtown while it awaits the opening of it’s new outdoor exhibit.

14. Roosevelt Beach 

Located in Theodore Roosevelt Memorial Park, Roosevelt Beach is a peaceful town beach overlooking Oyster Bay Harbor. There’s a public ramp for boats, and The Waterfront Center is located right outside the park for paddle boat rentals. Along the beach are perfect paths for rollerblading and biking. Cooper Bluff-Waterfront Bar is right next door if you’re looking to stop for a drink!

15. Bonus: Vanderbilt Museum & Planetarium (30 minutes from Oyster Bay) 

If you’re up for a 30-minute car ride, the Vanderbilt Museum in Little Neck is worth the visit. There’s so much to explore in the 1910 Spanish Revival estate, grounds, and gardens featuring exhibits on natural history, marine life, and ethnographic collections. Vanderbilt constructed several museum galleries with personal collections to host visitors around the world before it became a public space. 

There’s also a planetarium that puts on both daytime and evening shows, with laser shows taking place at night. If you purchase a ticket to the planetarium, it includes admission to the grounds of the Vanderbilt Mansion and exhibits, but tours will cost extra. 

Best Restaurants in Oyster Bay 

  • 2 Spring ★: Listed above.
  • Wild Honey ★:  One of our favorite restaurants in the area, serving creative American dishes with some fantastic seafood. Perfect for a romantic date with candlelight tables and cozy seating, located in the historic Moores building. 
  • Southdown Coffee: A charming coffee house serving award-winning coffee and hand-prepared lunch foods like paninis and salads. The location in Oyster Bay is on Audrey Ave, and they create such beautiful (and delicious) coffees, lattes, and more. 
  • Bonanza Stand: What might look like a simple ice cream shack is actually a lemon-ice legend and has been serving cold treats for over 100 years! It’s a small-town gem you have to hit, and they also serve hot dogs and other sides.  
  • Mill Creek Tavern (Bayville): Mill Creek is a great place for seafood, steaks, and other American dishes with a full bar and dining room. It’s one of the most popular restaurants in Bayville and only 7 minutes from downtown Oyster Bay.
  • Coach Meeting House: This was the famous restaurant during quarantine that was offering drive-thru margaritas and frosé! They still offer frozen drinks, but also are open for serving a mix of seafood, steak, pasta bowls and more. 

Where to Stay in Oyster Bay

  • The Inn at Fox Hollow: A boutique and tranquil hotel in Oyster Bay set on 8 acres of gardens along the North Shore with waterfalls. They have spa bathrooms and free amenities including an area shuttle, weekday dinner buffet and breakfast buffet, heated pool and a hot tub. 
  • Viana Hotel & Spa: This is Long Island’s only “green built” Feng Shui hotel with luxury services, a spa, and vibrant decor. It’s about 15 minutes from downtown Oyster Bay and also includes a steam room, gym, game room, indoor pool/hot tub, and an onsite restaurant serving Italian, Asian, and fusion dishes. 
  • Oheka Castle: This 1919 chateau-style estate is truly a unique stay, surrounded by lush gardens with antique rooms and a free continental breakfast. The dining rooms have fireplaces and chandeliers, and you can schedule in-room massages.  

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