We enjoy spotlighting different communities around Long Island, giving folks a punch list for an engaging and entertaining day trip. Steeped in history, teeming with activity, and loaded with natural beauty, the hamlet of Oyster Bay is a true pearl of Long Island.
Whether you're a resident, or you're looking for something new to do on the Island, you'll find lots to do, see, and eat in Oyster Bay. Enjoy museums, restaurants, shopping, parks, gardens, nature preserves, and rich waterfront boasting jam-packed events and activities to keep families busy. We have plenty of other day trip ideas and walkable downtown areas for you to visit as well.
Things to Do in Oyster Bay with Kids
Visitors can take a self-guided history tour through the village. The mile-long Oyster Bay History Walk squeezes 30 historic sites into one loop. Audio wands are available to pick up at the Oyster Bay Railroad Museum.
Speaking of the Railroad Museum, it is open on Saturdays and Sundays from 12pm to 4pm through mid-November. Located on Audrey Avenue, the museum is just around the corner from the historic train station. The Oyster Bay Rail Road Museum collects, preserves, and interprets the railroad heritage of Long Island. A wooden railway set is on display for children to play on, and there is a train whistle kids can't seem to get enough of blowing. Railroad artifacts and an electric train set are on view as well.
The Waterfront Center offers youth and educational water-based programs, as well as sailing and other watercraft rentals for jetting around Oyster Bay Harbor and the Long Island Sound. Kids can learn about the marine ecosystem in fun and engaging ways.
Built in 1883, The Waterfront Center's 60-foot oyster vessel Christeen is the oldest sloop in the country and a national landmark. Hop on board for a jaunt around historic Oyster Bay Harbor. Or enjoy an educational cruise, where kids can hoist the sails and take the helm. Just like a pirate's matey would!
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Drop a line into Oyster Bay Harbor and try for the catch of the day.
Oyster Bay is an ideal location to bring a fishing pole and drop a line. If you want a break from fishing, pack a picnic lunch, cycle, or skate along the harborfront park.
Boasting a beach, playground, boat launch ramp, and kayaks, this park neighbors The Waterfront Center and is open daily late June through Labor Day, then weekends only. Note that the beach is for Town of Oyster Bay residents and their guests only.
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Interactive exhibits at Planting Fields Arboretum explore its history and surrounding natural environment.
This sprawling, 400-plus-acre Gold Coast estate is full of tree tunnels, quaint cottages, fountains, and stately structures. Included on the National Register of Historic Places, the arboretum also has two lush greenhouses. Greenery and flowers of every color pack these glass houses from floor to ceiling. Hidden benches and nooks offer ideal thinking spots. Outside, the lawns are dotted with a variety of flowers, plants, and trees. Meander along a woodland path or pitch a picnic on the rolling lawn. The visitor center has an interactive museum exhibit about the estate's history, as well as a cafe. It also offers family programs. The park is open every day from 9am to 6pm, excluding December 25. The greenhouses are closed on Tuesdays for maintenance.
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Sagamore Hill is the historic home of our 26th president, Theodore Roosevelt.
The historic home of our 26th president, Theodore Roosevelt, from 1885 until 1919, this estate boasts 83 acres of lush nature trails, woodlands, beaches, a salt mash, and chicken coop. Sagamore Hill’s boardwalk nature trail leads to scenic water views of a salt marsh and beach. Snowshoesing, cross country skiing and sledding are permitted in winter. Bring Fido along because Sagamore Hill is dog friendly. NOTE: Access is increasing in a phased approach. Masks are required in all indoor locations. Park grounds, the beach, and all trails are open. The Theodore Roosevelt Home, the Summer White House, is open by advance reservation only.
Theodore Roosevelt died at Sagamore Hill in 1919 and was buried at nearby Youngs Memorial Cemetery. His grave is well-marked, as are those of family members, including Roosevelt's wife Edith. Fittingly for the nation's 26th president, 26 steps lead to Roosevelt's grave. The cemetery looks as it did in 1919.
A short walk from Youngs Cemetery is the Theodore Roosevelt Sanctuary, the country's first National Audobon Society songbird sanctuary. The 14-acre park is home to kingfishers, kingbirds, grackles, and goldfinches. How many can you spot? Take in the colors from among a host of native plant species.
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Visit Raynham Hall Museum and return to the Colonial era. Photo courtesy of the museum
TR dominates, but there is more to the history of Oyster Bay than the Roosevelts. Take Raynham Hall Museum, the 18th-century home of the Townshend family, who Long Island historians might recognize as part of Gen. George Washington's elaborate spy network. Visit the grounds and tour the museum for a look back at the role Oyster Bay played in the independence movement.
Seasonal Celebrations for Families in Oyster Bay
Pre-pandemic, few events brought Oyster Bay together more than the community's oyster celebration. Canceled in 2020 and 2021, organizers hope to bring the event back in October 2022. More than 150,000 guests have traditionally attended to enjoy live music, carnival rides, animals, and, of course, the flavorful oysters.
On Friday nights in the summer all are welcome to shake it to the music in front of Town Hall. There are even live dance demonstrations.
Visitors to Coe Hall can experience the magic of the holidays in this 1920s-era Gold Coast estate. Enjoy live jazz and hot cocoa as you tour the house, decorated for the season.
Shopping in Oyster Bay Village
This charming boutique offers curated clothing for parents and little ones, as well as eco-friendly toys, books, and some sweet and savory provisions.
The gift shop at Not Just Art carries art materials in every variety for all ages, as well as creative toys.
This store, on East Main Street, is a treasure, selling secondhand furniture and household items.
Where to Eat in Oyster Bay Village
Fuel up on java at Southdown Coffee and cruise Audrey Avenue on foot. Oyster Bay Brewing Co. has daily taproom hours if you're feeling hoppy. 2 Spring, Wild Honey and Coach Meeting House are all well-known Oyster Bay hot spots. Cafe Al Dente, The Homestead and Sweet Tomato offer a less fancy vibe. For a sweet treat, Ralph's and Carvel are nearby, but Bonanza's has been serving up Italian ices since 1889. It has an extensive menu of flavors, but lemon is still the best.
How to Get to Oyster Bay Village
The Long Island Rail Road's Oyster Bay branch stops right in Oyster Bay Village. If you're driving, take the Long Island Expressway to Exit 41 North and follow Route 106 north about 8 miles into the village.
A version of this post was first published in 2012. It was updated in October 2021.
Unless noted, photos are by the author.