What to Do in the Hamptons: 9 Must-Dos

You’ll find the Hamptons offers incredible experiences beyond expensive resorts—visit historic Montauk Point Lighthouse, relax at Main Beach or Cooper’s Beach, explore the Parrish Art Museum’s impressive collections, and tour local vineyards like Wölffer Estate. Don’t miss Sag Harbor’s maritime history, Jackson Pollock’s preserved studio, or affordable whale watching from Montauk. Add shopping in Southampton Village, hiking Hither Hills trails, and sunset e-bike tours for a complete experience that’ll show you everything this iconic destination truly offers.

Visit Montauk Point Lighthouse and State Park

Since you’re exploring the Hamptons, you can’t miss Montauk Point Lighthouse—it’s the oldest lighthouse in New York State and offers some of the best ocean views on Long Island. Built in 1796 under President Washington’s authorization, this 110-foot lighthouse sits dramatically on Turtle Hill at Long Island’s eastern tip.

You’ll get panoramic views of the Atlantic Ocean, Block Island Sound, and rocky coastline from the surrounding Montauk Point State Park.

The lighthouse museum, run by the Montauk Historical Society, provides fascinating insights into maritime history and local heritage. The lighthouse features a massive Fresnel lens that was recently restored and reinstalled in 2024 after being originally replaced in 1903.

Walk the coastal bluffs and explore the rocky shoreline for free—you only pay for lighthouse tours and museum admission.

It’s an affordable way to experience genuine American history while enjoying spectacular scenery.

Explore Main Beach and Cooper’s Beach for Classic Hamptons Shore Time

When you’re ready to experience the quintessential Hamptons beach scene, Main Beach in East Hampton and Cooper’s Beach in Southampton deliver everything you’d expect from world-class Atlantic shoreline.

Both consistently rank among America’s top beaches for their soft white sand, rolling surf, and upscale-yet-relaxed atmosphere.

You’ll find full amenities including lifeguards, restrooms, and snack bars during summer season (Memorial Day through Labor Day).

Cooper’s Beach offers chair and umbrella rentals, while Main Beach hosts evening bonfires and live music events like “Tuesdays at Main Beach.”

Expect daily parking fees and QR-code payment systems, so budget accordingly.

Both beaches support surfing, paddleboarding, and beach games. For a more serene experience, visit during October afternoons when the weather remains glorious but crowds have thinned considerably.

Their proximity to East Hampton and Southampton villages means you can easily combine shore time with dining and shopping.

Tour the Parrish Art Museum and LongHouse Reserve Sculpture Garden

After soaking up the sun and surf, you’ll find the Hamptons offers equally impressive cultural attractions that showcase world-class art without requiring a trip back to Manhattan. The Parrish Art Museum in Water Mill features works by Jackson Pollock, Willem de Kooning, and Roy Lichtenstein in Herzog & de Meuron’s stunning barn-inspired building.

At $20 for adults ($14 for seniors), it’s a worthwhile 1-2 hour investment, especially on Saturdays when docent tours are available at 2 PM. The museum offers free admission to visitors 18 and under, students with valid ID, veterans, and active-duty military personnel.

Don’t miss LongHouse Reserve’s 16-acre sculpture garden in East Hampton, where outdoor installations blend seamlessly with designed landscapes. Both venues emphasize American art with strong connections to Long Island’s artistic heritage, making them essential stops for culture seekers exploring the region’s creative legacy.

Take a Wine Tasting Day Trip to Wölffer Estate and Other Local Vineyards

The Hamptons’ wine scene rivals its beaches for pure enjoyment, and you’ll discover some of Long Island’s finest vintages without the Manhattan price tags.

Start your wine tour at Wölffer Estate Vineyard in Sagaponack, where tastings run $38-$55 per person. This 55-acre family-owned estate offers 75-minute guided tours with cheese and charcuterie pairings in their chic tasting room.

You’ll sample elegant merlots, pinot noirs, and vibrant rosés while enjoying vineyard views from their outdoor Wine Stand.

Create a three-stop experience by visiting nearby Channing Daughters Vineyard and Duckwalk Vineyard South. Channing Daughters features experimental blends using unique grapes like Muscat Ottonel, Malvasia, and Blaufränkisch alongside their classic varietals.

Pro tip: Visit during weekdays for smaller crowds and book guided group tours for up to 8 guests to maximize your tasting experience across multiple estates.

Walk Through Sag Harbor’s Whaling Museum and Historic Village

Beyond vineyard visits, Sag Harbor’s maritime past comes alive at the Whaling Museum, where you’ll explore America’s whaling heritage without breaking the bank. You’ll discover nearly 200 pieces of intricate scrimshaw—sailors’ folk art carved from whale teeth and bone—alongside authentic whaling tools and harpoons from the 1820s-1850s.

The museum occupies Benjamin Huntting’s 1845 Greek Revival mansion, featuring stunning Corinthian columns and hand-carved whale motifs. You’ll wander through four galleries showcasing over 3,500 artifacts, including a complete 1860s whaleboat and blubber processing equipment.

With affordable admission and seasonal hours, this National Register treasure welcomes 5,000+ visitors annually. You’ll gain authentic insight into maritime history while exploring the charming historic village surrounding this architectural gem. The museum’s mission bridges past and present, preserving and interpreting Sag Harbor’s rich cultural heritage while reflecting the vibrant village community of today.

Experience Jackson Pollock’s Studio at the Pollock-Krasner House

While many Hamptons attractions cost a fortune, you’ll find authentic artistic history at the Pollock-Krasner House, where Jackson Pollock and Lee Krasner created groundbreaking Abstract Expressionist masterpieces. Located on Springs-Fireplace Road, this National Historic Landmark offers guided tours for $20 (adults) or self-guided visits for $15.

You’ll walk through Pollock’s barn studio wearing protective slippers to preserve the paint-splattered floor where he created “Autumn Rhythm” and “Blue Poles.” The original drips and splatters remain exactly where Pollock left them.

Upstairs, you’ll see Krasner’s workspace, where she painted until 1984. The house remains as Krasner left it, complete with personal possessions, library, and record collection intact.

Reserve ahead for seasonal visits (May-October). The hour-long experience provides incredible value compared to other Hamptons activities, offering genuine artistic heritage without breaking your budget.

Go Whale Watching or Take a Sunset E-Bike Tour

When you’re ready to venture beyond the Hamptons’ beaches, whale watching tours from nearby Montauk offer an unforgettable maritime adventure that won’t drain your wallet. Viking Fleet’s 5-6 hour cruises cost just $85 for adults and $55 for kids, with marine biologists providing educational commentary as you search for humpback whales, finbacks, and dolphin pods.

Book between June and mid-September for the best sightings.

For a different perspective, try sunset e-bike tours through East Hampton’s scenic back roads and farmland. These 2-3 hour guided rides accommodate all fitness levels thanks to electric assist, letting you explore iconic landmarks while capturing golden hour photos.

Alternative whale watching options include New Hampshire-based Al Gauron’s 4-hour cruises starting at $55, which operate from June through September and provide excellent opportunities to spot minke whales, humpbacks, and dolphins.

Both activities offer unique ways to experience the Hamptons’ natural beauty without the typical high-end price tags.

Browse Southampton Village Boutiques and Tanger Outlets

After soaking up sun and sea air, you’ll find Southampton Village’s Main Street offers a delightful mix of high-end boutiques and local gems that showcase the Hamptons’ signature style. Browse between Jobs Lane and the ocean for everything from preppy resortwear at Gretchen Scott to stylish activewear at Bandier. Don’t miss Marina St. Barth’s colorful dresses or Flying Point Surf & Sport for beach essentials.

For budget-conscious shopping, head to Tanger Outlets Southampton in nearby Riverhead—it’s a 25-30 minute drive but worth it for discounted designer finds. With over 80 stores including Ralph Lauren, you’ll score quality pieces without the premium Village prices.

Whether you’re seeking statement jewelry at Jennifer Miller or home décor at historic Hildreth’s, Southampton satisfies every shopping style. Take a break from browsing to visit Golden Pear for their famous coffee and muffins, a popular celebrity hangout that’s perfect for refueling during your shopping adventure.

Hike Hither Hills State Park and Explore Local Nature Preserves

Beyond the manicured lawns and boutique shopping, Hither Hills State Park offers 1,755 acres of rugged natural beauty where you can explore 36 miles of trails without spending a dime. Start at the Hither Hills Overlook on Route 27 for spectacular sunset views. Then tackle the Fresh Pond trail—an easy 2.5-mile round trip perfect for families.

Don’t miss the Walking Dunes Trail, where you’ll witness sand formations slowly swallowing trees near Napeague Harbor. For history buffs, the coastal trail leads to Native American ruins with stone foundations connected to Montauk’s Stephen Talkhouse legacy.

Pack DEET-based repellent for ticks and mosquitoes, bring printed maps since cell service is spotty, and check hunting seasons before visiting. The park also features oceanfront camping for those looking to extend their stay and fully enjoy the natural surroundings.

The Sum Up

You’ll find the Hamptons offer something for every budget and interest. Mix free beach days with affordable hikes, then splurge on wine tastings or boutique shopping when you’re ready. Don’t miss the cultural gems like Pollock’s studio or the whaling museum—they’re reasonably priced and uniquely Hamptons. Pack snacks, bring sunscreen, and remember that timing your visit during shoulder seasons can save you money while still giving you that classic East End experience.