15 Of The Best Things To Do In Greenport, New York

Greenport is one of my favorite towns on Long Island’s North Fork. This small waterfront village has a little bit of everything I love about the area — historic streets, locally owned shops, great seafood, working marinas, and easy access to the North Fork’s vineyards, farms, and beaches.

My husband and I spent a year living nearby in Sag Harbor, and Greenport quickly became one of our favorite places to visit. We’ve returned many times since, and I especially love that there’s plenty to do while the town itself remains small and easy to explore.

Whether you’re stopping by for the day or spending a weekend on the North Fork, read on for all the best things to do in Greenport, New York.

The Best Things To Do In Greenport

Explore Downtown Greenport

Downtown Greenport is small and easy to explore on foot, with most of the village centered around Main Street, Front Street, and the waterfront.

Main and Front streets are lined with historic buildings housing local shops, restaurants, galleries, and cafes. From here, it’s only a few blocks to the harbor, where you’ll find Mitchell Park Marina, fishing boats, sailboats, and the ferry traveling back and forth to Shelter Island.

While you’re walking around, keep an eye out for the Village Blacksmith Shop on Front Street. The small shop has a working forge, and during the warmer months you can stop in to watch blacksmith demonstrations using traditional tools and techniques. It’s a quick stop, but such a unique piece of Greenport’s history.

I usually spend a good chunk of my time in Greenport just wandering around this part of town. Everything is close together, so it’s easy to explore without much of a plan.

Browse The Shops & Antique Stores

While you’re wandering around downtown, make time to pop into some of the shops along Main and Front streets. Greenport has a great mix of locally owned boutiques, antique stores, vintage shops, and places selling everything from clothing and jewelry to home goods and gifts.

There are plenty of boutiques scattered around downtown, so this is one of those places where I recommend browsing as you go rather than heading to just one specific shop. But if you’re looking for recommendations The Times Vintage is one of my favorites, with curated vintage clothing, home goods, jewelry, and a large collection of vinyl records. Nearby, Beall & Bell is another favorite for antiques and vintage finds, while Lydia’s Antiques & Stained Glass is packed with smaller pieces like glassware, pottery, artwork, and stained glass.

Relax At Mitchell Park & Ride The Antique Carousel

Just steps from downtown and right along the waterfront, Mitchell Park is a great place to relax for a bit while exploring downtown Greenport. The park has a large grassy lawn, picnic tables, and plenty of space to sit and enjoy views of the marina’s many boats.

There’s also a camera obscura and, most notably, Greenport’s antique carousel. The carousel dates back to the 1920s and eventually made its way to Greenport in the mid-1990s, where it’s been a favorite among families ever since.

Rides are inexpensive and the carousel is typically open daily during the summer, with more limited hours during the rest of the year. Check the current schedule before your visit, especially if riding the carousel is high on your list.

Mitchell Park also hosts community events and live music throughout the warmer months, so it’s worth checking the Greenport Village Calendar to see what’s happening during your visit.

Visit A Vineyard

The North Fork is one of New York’s best-known wine regions, with vineyards scattered throughout the narrow stretch of land between the Long Island Sound and Peconic Bay. So, naturally, wine tasting is one of the most popular things to do in the area.

Greenport itself is home to just one winery, Kontokosta Winery, located about 1.5 miles from downtown. The vineyard sits on a bluff overlooking the Long Island Sound, and the setting alone makes this one of my favorite wineries on the North Fork. Grab a glass or tasting, then head outside to enjoy the large lawn and beautiful water views.

If you want to explore beyond Greenport, there are plenty of other excellent wineries within a short drive. Macari Vineyards, Sparkling Pointe, Pindar Vineyards, Bedell Cellars, and McCall Wines are just a few of the most popular options.

Hours, reservation policies, and group restrictions vary between wineries, so I recommend checking directly with each vineyard before visiting — especially during busy summer and fall weekends.

Lavender By The Bay

Just a few minutes outside Greenport in East Marion, you’ll find Lavender By The Bay, a beautiful lavender farm with more than 80,000 plants spread across 17 acres.

The farm grows both English and French lavender, with bloom times varying throughout the summer. If you’re hoping to see the fields at their fullest, early July is typically your best bet, but I recommend checking the farm’s bloom updates before visiting since timing can change each year.

You can walk through the lavender fields, take photos, and stop by the farm shop for fresh and dried lavender, soaps, essential oils, and other lavender products. During peak bloom, admission is ticketed and weekends can get especially busy, so it’s a good idea to plan ahead.

If you’re visiting outside of lavender season, there are plenty of other seasonal farms to check out across the North Fork. Depending on the time of year, you’ll find everything from flower farms and strawberry picking to cherries, berries, apples, and pumpkins. Outside of winter and early spring, there’s almost always something in season.

Visit The Beach

Despite sitting on the water Greenport isn’t a major beach destination, but there are several beautiful spots around the village for swimming, relaxing, or simply spending some time by the water.

Fifth Street Park & Beach is located right in Greenport and has a small swimming beach, fishing pier, playground, picnic area, and volleyball court. For a little more space, Gull Pond Beach at Norman E. Klipp Park is just outside downtown and overlooks Shelter Island. It’s a popular swimming spot in summer and also has a playground and picnic areas.

One of the prettiest beaches in the area is 67 Steps Beach, a rocky stretch of shoreline tucked below a bluff. As the name suggests, you’ll reach the beach by walking down a long staircase, and once you’re there you’ll have beautiful views across the Long Island Sound. The shoreline here is rockier than some of the other nearby beaches, but it’s a gorgeous spot to spend some time by the water, especially around low tide.

For more of a traditional beach day, Orient Beach State Park is about 15 minutes east of Greenport. The park has a long shoreline along Gardiners Bay with generally calm water that’s popular for swimming, kayaking, and paddleboarding. There’s quite a bit more to do at the state park beyond the beach, which I’ll get into in a separate section below.

Parking Note: Beach parking around Greenport can be tricky since most local beaches require resident or town permits. To avoid parking issues, it’s often easiest to get a ride or bike to the beach. Orient Beach State Park, however, is the easiest option for visitors with a car since it’s a New York State Park with public parking available for an entrance fee.

Go For A Boat Tour 

If you want to get out on the water, there are plenty of opportunities to join a boat during your visit. You can book everything from a casual afternoon sail or sunset cruise to private charters and lighthouse tours.

East End Charters is one of the most popular options, offering both public sails and private charters from Greenport. Their public trips are typically two hours, with special options like brunch sails, live music cruises, and occasional wine cruises offered throughout summer. Private charters are available as well if you’re visiting with a group.

For something a little different, the East End Seaport Museum runs seasonal cruises to Bug Light, the lighthouse you’ll see just offshore from Greenport. These trips include the boat ride across Gardiners Bay and a chance to actually go inside the lighthouse, which is a pretty unique way to see it.

There are also private sightseeing cruises available around Shelter Island, Orient Point, and the surrounding waterways, including sunset and swimming trips.

Browse A Farmers Market Or Farm Stand

Farm stands are everywhere on the North Fork, and stopping at a few is one of my favorite things to do when I’m in the area. Depending on the season, you’ll find everything from berries, tomatoes, and sweet corn to fresh flowers, pumpkins, homemade pies, jams, and other local goods.

Right in Greenport, the Greenport Farmers Market takes place at Mitchell Park on Saturday mornings throughout the warmer months. It’s an easy stop while you’re already exploring downtown, with a mix of local produce, food, and goods from vendors around the area.

There are also plenty of roadside farm stands nearby. Most are small, so keep an eye out as you’re driving around, but if you’re looking for some of the larger options, Sep’s Farm in East Marion is one of the closest. You’ll find seasonal produce along with homemade jams, pies, prepared foods, and other local products. Latham’s Farm Stand in nearby Orient is another popular stop, especially if you’re heading toward Orient Beach State Park.

Seafood & Waterfront Dining

You can’t visit Greenport without having at least one meal by the water. The village has a long fishing and maritime history, so seafood is especially popular here, with everything from oysters and lobster rolls to locally caught fish.

Claudio’s Waterfront is probably the most recognizable option, with a large outdoor dining area right on the harbor. It’s especially fun in summer when the docks are busy and boats are constantly coming and going, they even have live music some afternoons and evenings. For something a little more casual, Little Creek Oyster Farm & Market is a great spot for oysters, local seafood, and drinks overlooking the water.

There are plenty of other waterfront restaurants around the harbor as well, so you won’t have trouble finding somewhere to grab lunch, dinner, or just a drink with a view. During summer weekends these spots can get very busy, so expect a wait during peak dining hours.

Visit A Museum

For such a small village, Greenport has a surprisingly good collection of museums, most focused on the area’s maritime and railroad history. Many are relatively small, so they’re easy to fit between other activities and are especially good options on a rainy day.

A few to check out include:

• East End Seaport Museum: Located right by the Shelter Island ferry, this small museum covers Greenport’s maritime history with exhibits on local lighthouses, fishing, shipbuilding, and the surrounding waterways. The museum also runs seasonal boat trips to Bug Light, which I mentioned above.
• Railroad Museum of Long Island: Greenport was once the eastern terminus of the Long Island Rail Road, and this museum explores that history through historic railroad equipment, artifacts, photographs, and exhibits.
• Fireboat Firefighter Museum: Housed aboard the historic Fire Fighter, a retired FDNY fireboat built in 1938. Visitors can board the vessel and learn about its decades of service in New York Harbor.
• Greenport Jail & Police Museum: A tiny museum inside Greenport’s former village jail, complete with original jail cells and exhibits covering the history of local law enforcement.
• Stirling Historical Society Museum: Set inside a historic Greenport home with exhibits, photographs, documents, and artifacts covering the history of the village and surrounding area.

Just outside Greenport, Horton Point Lighthouse in Southold is another great option. The lighthouse dates back to 1857 and has a small nautical museum inside, plus beautiful views over the Long Island Sound from the surrounding grounds.

Catch A Show At The North Fork Arts Center

Another good indoor activity is to see what’s happening at the North Fork Arts Center, located inside the historic Greenport Theatre on Front Street.

Movies are still a big part of the schedule, with a mix of new releases, classics, independent films, and special screenings, but there’s a lot more happening here now. The arts center also hosts live music and performances, dance, art exhibitions, lectures, workshops, and other community events throughout the year.

The nonprofit North Fork Arts Center took over the historic theater a few years ago, helping preserve the building while transforming it into a larger cultural arts space. It’s undergone quite a few renovations since then, with even more improvements set for completion this year.

Programming changes regularly, so check the North Fork Arts Center calendar before your visit.

Orient Beach State Park

About 15 minutes east of Greenport, Orient Beach State Park is one of the best places in the area to spend some time outdoors. We already touched on the beach above, but there’s quite a bit more to do here than swim.

The park sits along Gardiners Bay and has a mix of shoreline, salt marsh, and a rare maritime forest. There are nature trails to explore, plus opportunities for biking, fishing, kayaking, canoeing, and paddleboarding. Kayak, canoe, and paddleboard rentals are also available seasonally.

This is also a great spot for wildlife watching. Osprey, great blue herons, and egrets are commonly seen around the park, and there are four different lighthouses visible from the property, including Orient Point Lighthouse and Bug Light.

If you’re looking for even more outdoor space nearby, check out Arshamomaque Pond Preserve or Inlet Pond County Park, both located just a few miles from Greenport and offering peaceful walking trails, wildlife viewing, and plenty of natural scenery.

Seasonal Festivals & Events

Greenport hosts a variety of events throughout the year, but summer and fall are especially busy. From live music along the waterfront to festivals celebrating the village’s maritime history, these are a few of the most popular annual events to look out for:

• Blessing of the Fleet (mid June): This traditional maritime ceremony kicks off the summer fishing and sailing season, with local boats gathering in Greenport Harbor to receive a blessing for a safe season on the water.
• Dances in the Park (Mondays in summer): One of Greenport’s longest-running summer traditions, with free live music at Mitchell Park every Monday evening. Bring a blanket or lawn chair and enjoy the music along the waterfront.
• Greenport Fire Department Carnival & Fireworks (Late June / Early July): A classic summer carnival with rides, games, food, and fireworks running from late June to the Fourth of July.
• Shakespeare in the Park (select dates in July): Northeast Stage puts on free outdoor Shakespeare performances around the North Fork each summer, including shows at Mitchell Park in Greenport.
• Greenport Maritime Festival (late September): Greenport’s biggest annual event celebrates the village’s maritime history with a full weekend of festivities throughout downtown. The event includes a maritime parade, live music, local vendors, food, family activities, and fun traditions like the Cardboard Boat Race.

These are just a few of the bigger annual events, check the Village of Greenport calendar before your visit to see what’s happening while you’re in town.

Ferry To Shelter Island 

Okay, this one technically isn’t in Greenport, but the ferry to Shelter Island leaves right from downtown, so visiting the island is a very popular addition to a Greenport itinerary. The ferry ride takes less than 10 minutes, and you can cross as a walk-on passenger or bring your car.

I’d strongly recommend bringing your car if you actually want to explore the island. Shelter Island is bigger than it looks and attractions can be surprisingly spread out. Biking is definitely an option, but expect to cover some decent distances if you want to see more than the area around the ferry.

Once you’re there, you can hike at Mashomack Preserve, kayak, spend some time at Crescent Beach or Wades Beach, browse the small shops, stop by the brewery, or grab something to eat. I especially love Black Cat Books, a used bookstore housed inside a historic building.

To really make the most of Shelter Island, I’d plan on spending at least half a day, if not a full day, exploring. That said, you can also bring your car over, drive around for an hour or two, and get a feel for the island before heading back to Greenport.

The North Ferry runs frequently throughout the day and reservations aren’t required. Just be sure to bring cash — the ferry is cash only.

Explore The Nearby North Fork Towns

Greenport is just one of several small towns and hamlets scattered across the North Fork, so if you have extra time, it’s worth exploring beyond the village. Southold, Cutchogue, Mattituck, East Marion, and Orient are all nearby, and you’ll pass plenty of vineyards, farm stands, and small local businesses as you drive between them.

Southold is one of my favorite stops, with a small downtown, historic sites, and Horton Point Lighthouse Nautical Museum overlooking the Long Island Sound. Farther west, Mattituck has more shops and restaurants, along with popular farm stops like Harbes Family Farm.

Most of these require a half or full day to explore.

Greenport is easily one of my favorite places to visit on the North Fork. Between the waterfront, shops, vineyards, beaches, and easy access to the rest of the area, there’s plenty to keep you busy without the town ever feeling overwhelming.

I hope you have the best time exploring Greenport and the North Fork!

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