Oyster Bay sits on the North Shore of Long Island, about 35 miles east of Manhattan, nestled in a harbor that has been at the center of American history since the 1600s. The town was a British stronghold during the Revolution, home to one of Washington's most important spy networks, a summer retreat for the 26th president, and a showcase for the Gold Coast estates that defined American wealth at the turn of the 20th century.

Most visitors come for Sagamore Hill and leave not realizing how much else is here. This guide covers every major historic site in and around the village — what each one is, why it matters, and how to build a full day that does justice to all of it.

And when you're done? Oyster Bay Brewing Co. is right here on Audrey Avenue. We've been in this village since 2012 and we'll be the first to tell you — this is one of the best day trips on Long Island.

Stop 1 · 20 Sagamore Hill Road

Sagamore Hill.
The Summer White House.

Sagamore Hill was Theodore Roosevelt's home from 1885 until his death in 1919, and during his presidency it served as the working seat of the American government every summer — earning the nickname the Summer White House. He received foreign dignitaries here, negotiated the treaty that ended the Russo-Japanese War (winning him the Nobel Peace Prize in 1906), wrote 18 of his 35 books, and raised six famously spirited children on these 83 acres above Oyster Bay harbor.

The house is preserved exactly as it was when he lived in it — not restored, not reimagined. The trophies on the walls are the trophies he hung. The books on the shelves are the books he read. Walking through Sagamore Hill is one of the most authentic presidential experiences in the country.

Address: 20 Sagamore Hill Road, Oyster Bay

House tours: Friday–Sunday, $15 adults · Grounds free daily, sunrise–sunset

Tickets: recreation.gov · nps.gov/sahi

Stop 2 · 30 West Main Street

Raynham Hall.
Where Spies Saved a Revolution.

Built in 1738, Raynham Hall is one of the most historically significant homes on Long Island — and one of the most underrated anywhere in America. During the Revolutionary War, British general John Simcoe quartered his Queen's Rangers here, essentially occupying the home of the Townsend family. What Simcoe didn't know was that Robert Townsend — son of the house — was secretly operating as one of George Washington's most valuable spies.

Robert Townsend was "Culper Junior" in Washington's famous Culper Spy Ring — a network of Long Island operatives that provided intelligence from British-occupied New York. Intelligence from the Culper Ring is credited with exposing the treason of Benedict Arnold and preventing a British ambush that could have changed the course of the war. It all flowed through this house on West Main Street.

The house is now a museum featuring period rooms furnished with over 5,000 authentic 18th and 19th century artifacts. It is the only historic house museum on Long Island accredited by the American Alliance of Museums — a distinction it has held since 1991. Self-guided tours use the 1776AR augmented reality app to put you in the middle of the Revolution; guided tours go deeper into the Townsend family story.

Don't miss: The exhibition on the 19 enslaved African Americans who lived in the Townsend household — a frank and important part of the story that the museum tells with real care.

Stop 3 · 1395 Planting Fields Road

Planting Fields Arboretum.
409 Acres of Gold Coast Beauty.

If Sagamore Hill is the political soul of Oyster Bay and Raynham Hall is its revolutionary conscience, Planting Fields is its aesthetic crown. This 409-acre estate was developed by insurance magnate William Robertson Coe and his wife Mai from 1913 onward, and it represents the Gold Coast at its most extravagant and most beautiful.

The landscape was designed by the Olmsted Brothers — the same firm responsible for Central Park. More than 160 acres of formal and informal gardens, five miles of woodland trails, and collections that include over 600 varieties of rhododendrons and azaleas make this one of the finest arboretums in the Northeast, open year-round.

At the center of it all is Coe Hall — a 65-room Tudor Revival mansion that was the Coe family's private residence until 1955. Guided tours run April through September and walk you through rooms that still feel as though the family just stepped out. The scale and quality of the interiors are genuinely shocking for an arboretum day trip.

Best time to visit: late May through June for rhododendrons and azaleas in peak bloom. The woodland trails are spectacular year-round and great with dogs (on leash).

Stop 4 · Cove Road, Oyster Bay

Theodore Roosevelt
Sanctuary & Audubon Center.

Established in 1923 in Theodore Roosevelt's memory, this 12-acre woodland is the oldest songbird sanctuary in the United States. It was created four years after TR's death by the National Association of Audubon Societies as a living tribute to one of America's greatest conservationists — the man who established five national parks, 18 national monuments, and protected over 230 million acres of public land during his presidency.

The sanctuary sits just down the road from Sagamore Hill and includes woodland trails, native plant gardens, live raptors on display, and, most movingly, the gravesite of Theodore Roosevelt himself. Visiting TR's grave at Young's Memorial Cemetery — a simple headstone in a quiet grove — after touring his home and presidential legacy is one of the most unexpectedly affecting experiences in American historical tourism.

The Audubon Center offers environmental education programs and is an excellent stop for families with young children. Entry is free, making it the kind of place you walk into expecting to stay 30 minutes and end up staying two hours.

Stop 5 · 1 Railroad Avenue

Oyster Bay Railroad Museum.
TR's Personal Train Station.

Built by the Long Island Rail Road in 1889, the Oyster Bay Railroad Station was the personal station of Theodore Roosevelt for the years he lived at Sagamore Hill. The president arrived and departed from this platform on matters of state, vacation, and family. The station served passengers for 110 years until 1999 and is now a landmark building on the National Register of Historic Places.

The Oyster Bay Railroad Museum operates two locations within walking distance of each other through Theodore Roosevelt Memorial Park: the restored historic station itself, and an outdoor rail yard featuring Locomotive #35 and a collection of historic rolling stock. Visitors can experience a turntable ride, operate locomotive and diesel simulators, and download the TRAR augmented reality app for an immersive TR-guided tour through the station's history.

A great stop for families — kids can sit in the locomotive cab, operate the simulators, and ride the turntable. The two-location layout means a short scenic walk through the park between stops.

Beyond the Museums

The village itself
is worth the walk.

Audrey Avenue — Oyster Bay's main street — has been the commercial heart of the village for well over a century. Today it's lined with independent shops, restaurants, and a handful of places that tell their own piece of the story.

Theodore's Books at 17 Audrey Avenue is owned by former Congressman Steve Israel and named for the president whose presence still defines this village. The selection of TR-related books is exceptional. Pick one up before heading to Sagamore Hill and you'll read it a different way.

Southdown Coffee at 49 Audrey Avenue was named one of the best coffee shops in America by Food & Wine. Worth a morning stop before the day begins.

Theodore Roosevelt Memorial Park and Beach sits at the foot of Audrey Avenue and offers harbor views, picnic areas, and a beach that has been the village's gathering spot for generations. It's also where the Oyster Bay Cruise Nights fill the block every Tuesday from May through September — classic cars, live music, and the whole community out on a summer evening.

The Perfect Day

How to do Oyster Bay
in a single day.

End Your Day Here

14 years on Audrey Avenue.
Cold beer brewed here.

You've spent the day walking through 300 years of American history. Come pull up a stool and tell us what you saw. We've been a part of this village since 2012 and we love hearing from people who are discovering it for the first time.

36 Audrey Avenue · Oyster Bay, NY · Open 7 days
Friday & Saturday till midnight · No reservation needed