The quiet hamlet of Oyster Bay has much to offer the urban day tripper, especially if that day tripper turns out to be a nature lover. The town itself is perched on the shore of Oyster Bay Cove, which is a protected inlet with some of the purest waters in Long Island Sound. From the shore, visitors have a great view of the tree-lined beaches of Center Island. During World War II, the Jakobson Shipyard employed over 600 hundred workers who built tug boats and mini-submarines for the Navy. Today, the shipyard is closed, but a lingering maritime atmosphere greets you as you step off the train and take in the small harbor filled with boats of all shapes and sizes.
Nearby is Sagamore Hill, Theodore Roosevelt’s retreat that was once nicknamed the ‘Summer White House’ and beyond that is the vast Oyster Bay National Wildlife Refuge. In town, there are plenty of shops and restaurants to check out, but you will instantly fall in love with Bonanza’s—an Italian Ice stand that sells just about everything from chili dogs to mozzarella sticks.
Recently, oM found you could bring a bike and see it all on a budget of $40. Below is our itinerary for a day out in Oyster Bay.
Getting There and Back: $16.50
Take the Long Island Railroad off peak for a round trip cost of $16.50. We suggest bringing your bike (lifetime pass/$5) in order to tour the area. The only other option out to Sagamore Hill and the Wildlife Refuge, about three miles from the town of Oyster Bay, is a costly cab ride.
Free and cheap things to do
Roosevelt Museum at Old Orchard | 20 Sagamore Hill Road | nps.gov
Though the house on Sagamore Hill is closed for renovations, the Roosevelt Museum and the grounds surrounding it are still open. The museum itself is free and filled with great artifacts from President Theodore Roosevelt’s life. Take time on your visit to have a history lesson.
Oyster Bay National Wildlife Refuge | Cove Neck, NY | fws.gov
The Wildlife Refuge is a wetlands heaven. The area consists of over 3,000 acres of bay, marsh and wetland. This means tons of birds. From waterfowl to raptors, the Refuge’s website boasts over 100 species in the park. It’s also beautiful out there and deserving of a photoshoot, so bring binoculars and a camera.
Waterfront Center | 1 West End Ave. |
The beach at Oyster Bay stays bustling thanks to the work of the non-profit WFC, The Waterfront Center for Education and Recreation. There is a long dock that extends deep into the bay. Take a walk along the dock and observe kayakers (or join them for $20/hour) and sailors. Grab a seat on one of the benches or somewhere next door in Theodore Roosevelt Memorial Park and have a Bonanza picnic (see below) before you say good-bye to Oyster Bay and head back to the city.
Where to eat
Bonanza’s | $1.25 – 8.50 | 25 Shore Avenue | bonanzasofoysterbay.com
The rest of your $40 budget has been saved for a stop off at Bonanza’s on the way back to the train. This little Italian ice stand has its own history. Proprietor Chick Bonanza started selling Italian Ices from a cart in Brooklyn when he first arrived to the US in the early 1900’s. Four generations later, his great grandson is running the show and little has changed. Here you can get Italian ices for quite the bargain as well as lunch items like hot dogs, chicken tenders and onion rings for well under ten dollars.
Photos: Friends of the Bay and Roosevelt Museum
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Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram