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North Fork Travel Guides

The Ultimate North Fork of Long Island Travel Guide: What to Do in May

April 20, 2025

Nestled between the Long Island Sound and the Peconic Bay, you’ll find the North Fork of Long Island. It is a charming getaway brimming with natural beauty, quaint towns, and countless adventures. May is one of the best months to visit this scenic part of Long Island. Spring on the North Fork offers mild weather, vibrant blooms, and a variety of outdoor activities. Whether you’re a wine lover, outdoor enthusiast, or history buff, the North Fork has it all. Here’s your comprehensive travel guide to what to do on the North Fork in May.

1. Sip Local Wines at the North Fork Wineries

May marks the beginning of the wine-tasting season on the North Fork. You’ll find no better way to kick off your stay than the region’s world-class wineries. The North Fork, part of Long Island Wine Country, is home to over 30 vineyards and wineries. Explore the many tasting rooms, events, and curated experiences happening across the region. Enjoy the picturesque views of stretching toward the horizon as you sip on award-winning wines.

Cheers from Oregon Rd

Wineries to Visit:

  • Macari Vineyards – Macari Vineyards is a family-owned winery that offers an inviting, laid-back experience and breathtaking scenery, Macari Vineyards is perfect for a relaxing afternoon.

  • Suhru & Lieb Vineyards – With a focus on high-quality, sustainably grown grapes, Suhru & Lieb Vineyards offers estate-grown, award winning wines, with a covered Patio overlooking rolling farmland, making it a perfect spot to relax and enjoy a glass.

  • Lenz Winery – Known for its exceptional Bordeaux-style wines, Lenz Winery offers a variety of red, white, and sparkling wines, all crafted with care. The winery’s inviting tasting room and spacious grounds provide a peaceful setting to enjoy their wines and the beautiful surroundings.

2. Explore the Scenic Outdoors: Hiking and Biking

May brings warm weather to the North Fork, making it an ideal time to explore the region’s beautiful landscapes. Whether you prefer hiking, cycling, or simply strolling through scenic areas, the North Fork offers plenty of outdoor activities to choose from.

Hiking Trails to Explore:

  • Arshamomaque Preserve – Located in Southold, the Arshamomaque Preserve offers serene hiking trails that wind through wetlands, woodlands, and meadows. This peaceful nature reserve is perfect for those looking to connect with nature. The preserve’s easy-to-navigate trails make it a great spot for a leisurely hike.
  • Mashomack Preserve – For a more immersive nature experience, head to Mashomack Preserve in Shelter Island. This 2,000-acre preserve features a mix of salt marshes, forests, and tidal creeks. The hiking trails here range from easy to moderate, making it an ideal destination for both beginners and experienced hikers.

Biking:

  • Rent a bike and explore the peaceful country roads that wind through vineyards and farms. The flat terrain and beautiful surroundings make the North Fork a biker’s paradise.

3. Visit the Charming Towns of the North Fork

The North Fork is made up of several charming small towns, each with its unique vibe and all worth a visit! May is a great time to window show and wander about town as  they are less crowded than during the peak summer months.

  • Greenport – Known for its historic waterfront, Greenport is a quaint, picturesque village where you can stroll along quiet streets, enjoy artisanal shops, and dine at fantastic local restaurants. Don’t miss the Greenport Carousel, a fun, family-friendly stop that has been part of the town’s charm for over 90 years.

  • Mattituck – A quiet village with a mix of farmstands and vineyards, Mattituck is great for a relaxing day of shopping and dining. Be sure to check out the famous Love Lane for its boutiques and cafes.

  • Cutchogue – A hidden gem, Cutchogue is a peaceful village, perfect for a slower pace. Known for its lovely vineyards and farm stands, it’s an ideal spot to enjoy the region’s agricultural offerings. The town has a rich history, and you can visit the historic Cutchogue Village Green and its surrounding landmarks.

  • Orient – For a truly relaxing experience, visit the historic town of Orient. You can explore its charming downtown, hike to the Orient Beach State Park. Or enjoy a quiet picnic at Orient Point Park.

4. Attend Local Festivals and Events

May is the start of the season on the North Fork. There are plenty of events happening throughout the month. Whether you’re into food, wine, or arts and crafts, there’s something for everyone to enjoy. Keep an eye on the Northforker website for weekly upcoming events!

Must-Visit May Events:

  • Greenport Farmers Market (Open May) – A great spot to pick up fresh, locally grown produce, handmade goods, and artisanal treats. It’s the perfect place to get a taste of the North Fork’s agricultural bounty.

  • Greenport Cherry Blossom Walk (Early May) – Check out the beautiful cherry blossom trees that line the streets of the village while they’re in full bloom using the map provided by the village for a self-guided tour.

Each spring, Greenport bursts into color as its beloved cherry blossom trees come into full bloom, transforming the charming village into a pink-and-white dreamscape. These blossoms, typically peaking in late April to early May, line the streets and parks, creating an inviting and whimsical atmosphere perfect for strolls, photos, and picnics. Locals and visitors alike flock to the area to witness the fleeting beauty of the blossoms, which have become a cherished seasonal tradition and a symbol of renewal and community spirit in this scenic North Fork town.

5. Relax by the Beach

The North Fork boasts beautiful beaches that are perfect for a peaceful day by the water. While the water might still be a bit chilly in May, it’s an ideal time for beach walks, picnics, or just soaking in the coastal views.

Top Beaches to Visit in May:

  • Orient Beach State Park – With its stunning views of Gardiners Bay, Orient Beach State Park offers peaceful walking paths and sandy shores to explore. It’s a great place to relax and take in the natural beauty of the North Fork.

  • Truman’s Beach – Located in the charming town of Southold, Truman’s Beach is known for its tranquil atmosphere. The beach features beautiful sandy shores and clear waters, making it a perfect spot to unwind and enjoy the serene surroundings. It’s also a great location for a peaceful picnic or a quiet walk along the coastline.

6. Farm Fresh Fun: Visit a Local Farm Stand

May marks the start of farm-fresh produce on the North Fork, and many farm stands begin opening for the season. Stop by a local farm stand to pick up fresh produce, homemade jams, and baked goods straight from the farm.Catapano Dairy Farm Goat in the window

Popular Farm Stands:

  • Sang Lee Farms – Known for its organic vegetables, Sang Lee Farms offers seasonal produce, as well as ready-to-eat dishes made with their farm-fresh ingredients.

  • Harbes Family Farm – A family-friendly spot where you can pick your own fruits (like strawberries in May), visit farm animals, and enjoy the farm’s delicious homemade pies.

  • Catapano Dairy Farm – Located in Southold, Catapano Dairy is a must-visit for cheese lovers. They offer fresh, locally made goat cheese and dairy products, perfect for a unique, tasty experience. The farm also has a petting zoo, making it fun for families.

  • Wickham’s Fruit Farm – A beloved stop for fresh produce and farm goods, Wickham’s offers everything from strawberries to freshly baked donuts. It’s a great place to grab fresh ingredients for a picnic or to enjoy the season’s first crops.

7. Enjoy a Scenic Boat Tour or Fishing Trip

The waters surrounding the North Fork are perfect for outdoor exploration. Whether you’re into boating, fishing, or simply relaxing on the water, there are many ways to enjoy the region’s maritime beauty.

  • Boat Tours – Take a relaxing boat tour around Greenport Harbor or Peconic Bay for breathtaking views and local wildlife.

  • Fishing – May is a great time for fishing on Long Island, with abundant catches of striped bass and bluefish in local waters. Several local charters offer half-day or full-day fishing trips.

8. Discover History and Culture

The North Fork is rich in history, and May is an ideal time to explore the area’s historical sites. Learn about the region’s maritime heritage, visit museums, and explore historic homes.

Top Historical Spots:

  • The Railroad Museum of Long Island – Located in Greenport, this museum is dedicated to preserving the history of Long Island’s railroad system. Visitors can view historic trains, learn about the history of the Long Island Rail Road, and even take a ride on a vintage train.

  • The East End Seaport Museum – Also in Greenport, this museum highlights the maritime history of the region, showcasing artifacts from the area’s seafaring past.

May is a wonderful time to visit the North Fork of Long Island. With pleasant weather, vibrant blooms, and a mix of outdoor activities, local festivals, and historical sites, there’s no shortage of things to do. Whether you’re exploring local wineries, hiking through scenic landscapes, or relaxing at the beach, you’re sure to find plenty of activities to make your visit unforgettable. So pack your bags, put on your best spring outfit, and get ready for an amazing North Fork adventure this May!

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