Top 5 Things to Do Near Oyster Bay — Where Luxury Living Meets Local Charm

If you’re exploring homes or building your next chapter on Long Island’s North Shore, the neighborhood around Oyster Bay deserves your attention. From historic landmarks and fine dining to scenic parks and family-friendly attractions, Oyster Bay offers a lifestyle that perfectly blends luxury, leisure, and local charm.

And if you’re ready to make this lifestyle your own, check out two brand-new homes now available on Mylestone Home:

• 758 Connecticut View Dr, Oyster Bay, NY

• 762 Connecticut View Dr, Oyster Bay, NY

1. Visit the Sagamore Hill National Historic Site

Step into presidential history at Sagamore Hill, the summer home of Theodore Roosevelt. Nestled among lush woodlands, this estate offers guided tours, nature trails, and stunning coastal views — the perfect weekend activity for those who love a mix of history and fresh air.

2. Explore the Oyster Bay Railroad Museum

A hidden gem for locals and visitors alike, the Oyster Bay Railroad Museum celebrates the town’s rich connection to the golden age of rail travel. Tour restored train cars, step inside Roosevelt’s private railcar, and get a glimpse of how Oyster Bay helped shape Long Island’s development. It’s family-friendly, educational, and full of charm — a must-see stop before grabbing lunch in town.

3. Dine at 2 Spring Restaurant

Located right in the heart of Oyster Bay, 2 Spring delivers an upscale dining experience that rivals any Manhattan hotspot. Known for its creative menu, elegant atmosphere, and impeccable service, it’s a go-to for locals celebrating special occasions — or just living their best life on the North Shore.

4. Stroll the Gardens at Planting Fields Arboretum

Just minutes away, Planting Fields Arboretum offers 400 acres of botanical gardens, manicured lawns, and wooded trails. The historic Coe Hall mansion makes for an unforgettable backdrop to any weekend outing. If you’re a fan of timeless architecture and outdoor beauty, this destination feels like a living design inspiration board.

5. Discover Downtown Oyster Bay & the Waterfront

Charming boutiques, cozy cafés, and water views make Downtown Oyster Bay a local favorite. Spend your afternoon browsing the shops, grabbing coffee by the bay, or taking in the view from Theodore Roosevelt Memorial Park. It’s where community, coastal living, and convenience all meet.

🏡 Your Oyster Bay Lifestyle Awaits

From history buffs and nature lovers to foodies and families, Oyster Bay has something for everyone — and that’s what makes it one of Long Island’s most sought-after neighborhoods.

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