Things to Do in Oyster Bay, NY: A Local's Guide to the Gold Coast

If you do one thing in Oyster Bay, make it Sagamore Hill. Theodore Roosevelt lived here from 1885 until his death in 1919, and during his presidency it served as the Summer White House — hosting foreign dignitaries, campaign speeches, and the peace talks that ended the Russo-Japanese War. The 23-room Queen Anne shingle-style mansion is remarkable on its own, but what sets Sagamore Hill apart is that nearly 95% of the furnishings are original to the house. Walking through it feels genuinely lived-in rather than staged. The grounds are free and open every day from sunrise to sunset. Ticketed tours of the interior run Wednesday through Sunday — come early, as tickets are first-come, first-served and sell out regularly. The Theodore Roosevelt Museum at Old Orchard is free and worth a visit before or after the house tour.

Raynham Hall is a 1738 colonial home right in the heart of downtown Oyster Bay with a story that sounds more like a spy thriller than a history lesson. This was the home of the Townsend family — and Robert Townsend served as George Washington's secret agent, operating as a key member of the Culper Spy Ring. The intelligence network he helped run played a significant role in turning the tide of the Revolutionary War. The museum's period rooms are furnished to reflect both 18th and 19th century life, and the knowledgeable, costumed staff bring the history to life in a way that sticks with you. It's the only historic house museum on Long Island accredited by the American Alliance of Museums — a distinction it's held since 1991. Open Tuesday through Sunday, 1–5 PM.

Just a five-minute drive from downtown, Planting Fields is a 409-acre former Gold Coast estate landscaped by the Olmsted Brothers — the same firm responsible for Central Park. The grounds feature over 20 distinct gardens, five miles of woodland trails, and two spectacular greenhouses. Coe Hall, a 65-room Tudor Revival mansion at the heart of the property, was the home of insurance magnate William Robertson Coe and his wife Mai, daughter of a Standard Oil executive. The grounds are open year-round, every day from 9 AM to 5 PM, with free admission. Spring is the peak season — the rhododendrons, azaleas, and camellia collection (over 300 plants, many originally imported from England) are breathtaking. If you only have an hour, walk the greenhouse loop and the Italian Garden.

Oyster Bay has a long maritime history, and the WaterFront Center is where you can connect with it directly. Sitting right on the harbor at Theodore Roosevelt Memorial Park, this non-profit offers sailing lessons for all levels, paddleboard and kayak rentals, and harbor tours aboard CHRISTEEN — a 138-year-old oyster sloop that is the oldest working vessel of its kind in the United States. Even if you're not on the water, the park is one of the best spots in town to sit, watch the boats, and actually decompress. Rentals available daily, 9 AM–8 PM.

Start your day right. Southdown has been one of Long Island's most respected specialty coffee roasters since 2014 — earning a spot in Food & Wine's best coffee shops in America and taking national recognition at the 2019 US Coffee Roasters Championship. Their Oyster Bay location sits right on Audrey Avenue, steps from the brewery. Every item on the menu is hand-prepared, pastries are delivered fresh daily from local bakers, and the coffee is ethically sourced and locally roasted. Whether you need a quick espresso before Sagamore Hill or a proper sit-down morning, this is your spot. Open every day 7 AM–6 PM.

The crown jewel of the Oyster Bay dining scene. Chef Jesse Schenker — an Iron Chef winner who built his reputation at Recette and Gander in New York City, and has been named one of the country's best young chefs by both Forbes and Details — delivers tasting menus and multi-course dinners with the kind of precision you'd expect from a top NYC restaurant, not a North Shore village. Reviewers consistently call it one of the best dining experiences on Long Island. The menu changes regularly and centers on premium, in-house-prepared ingredients. Make a reservation — this one books up.

Sharing the Snouder's Building with L'Étoile, Provisions is a chef-driven specialty grocery and gourmet market operated by Lush Life Group. Fresh bread and baked goods from Provisions Bread & Cheese arrive daily, coffee comes from New York-based For Five Coffee Roasters, and the shelves are stocked with curated specialty foods and housewares you won't find at a typical grocery store. It's a great stop for picking up something to take home or putting together a picnic before heading to Planting Fields. After hours, Provisions transforms into "The Dinner Table at Provisions" — a reservation-only, family-style dining experience for up to 10 guests, with meals built around signature market recipes. A genuinely unique addition to Oyster Bay. Open Monday through Friday 10 AM–7 PM, weekends 9 AM–6 PM.

The Audrey is Oyster Bay's all-day destination — and it genuinely earns that description. By day, it's a relaxed café atmosphere with coffee, breakfast, and lunch. By evening, the space shifts into a vibrant kitchen and bar with a meticulously curated global wine list, crafted cocktails, and elevated comfort dishes. Favorites include the burrata with prosciutto, Bruschetta Caprese, and inventive flatbreads like Prosciutto and Truffle & Mushroom. The outdoor patio is a prime spot in warmer months. From Stellina Hospitality, the same group behind L'Étoile and Gioia.

Oyster Bay's newest and most buzzed-about arrival. Dough & Co. built its reputation in Huntington starting in 2022 — where it quickly earned a following and was named one of the top three pizzerias in the Tri-State area by The Washington Post — before opening at 25 East Main Street in early 2026. Owner Danny Rocca's philosophy is uncompromising: exceptional dough, no shortcuts. The cold-fermented crust is light, airy, and crispy in all the right ways, and the burrata slice is already the best seller at the new location. To-go focused, open seven days a week for lunch and dinner.

An Oyster Bay institution since 1896 — which predates Teddy Roosevelt's presidency, which means there's a reasonable chance the man himself ate here. The Homestead is pure comfort food, cold drinks, and a setting that feels like it's genuinely been there forever, because it has. The burger is consistently praised as one of the best in town. Live music on Fridays and Saturdays, open jam night every Wednesday, and a back patio that opens up through the warmer months. The kind of place every town needs and few actually have.