For an unforgettable dining experience, guests of The Harbor Front Inn are invited to dine at The Halyard, Greenport’s premier coastal seafood restaurant. Known for its fresh, locally-sourced ingredients, The Halyard offers exquisite dishes paired with stunning views of Long Island Sound. Whether for brunch or dinner, enjoy a perfect meal in a serene coastal setting.

Since 1987, Aldo’s Coffee has been a Greenport staple, offering small-batch, organic coffee roasted fresh daily. Pair your coffee with freshly baked pastries like almond croissants and blueberry muffins. Whether you’re stopping by for a quick pick-me-up or taking some home, Aldo’s commitment to quality and local craftsmanship is unmatched, making it the perfect spot to experience the heart of Greenport.

North Fork Brewing Company is dedicated to creating craft beer anchored in our rich North Fork traditions of agriculture, hard work, and good times.

Local brewery who’s beer highlights multiple aromatic hops – creating a smooth & balanced taste and clean finish.

With two distinct locations on the North Fork, Greenport Harbor Brewing Co. invites you to experience craft beer at its finest. Visit the original tasting room in a renovated 1860s firehouse in the heart of Greenport Village, or head to the spacious Peconic brewery, where rolling fields, live music, and a seasonal beer garden set the scene. Both offer flavorful, small-batch brews—and a perfect taste of local life.

Located in the heart of Greenport Village, Mitchell Park is a lively waterfront gathering place featuring the Greenport Marina, a charming antique carousel, a seasonal ice skating rink, and the one-of-a-kind Camera Obscura. It’s a perfect spot to stroll, play, and take in sweeping views of the harbor.

A beloved local gem, this fully refurbished 7,000-square-foot roller rink blends nostalgic charm with fresh energy. Lace up your skates and glide beneath the lights in one of Greenport’s most unique and family-friendly venues.

Hallockville Museum Farm is a not-for-profit (501 (c)3) organization dedicated to take Long Island back to its family farming roots and explore their relevance today. Hallockville Museum Farm offers museum tours, classes and workshops.

Island’s End Golf is an 18 hole facility located in the heart of Wine Country on the North Fork of Long Island.

Cycle around Shelter Island and find semi-secret beaches, beautiful homes and a charming town center.

This scenic preserve offers peaceful trails, wildlife-rich wetlands, and over 2,200 feet of shoreline along the pond. With trailheads and outlooks throughout, it’s an ideal spot for a quiet walk, birdwatching, or simply soaking in the beauty of the North Fork.

Orient Point is the easternmost town on Long Island’s North Fork—a small hamlet with a quaint village, open skies, and quiet charm. It’s the perfect place for a scenic drive, a peaceful beach walk, or catching the ferry to Connecticut.

Set on a nearly 500-acre vineyard and farm in Mattituck, Macari Vineyards offers a range of guided tasting experiences led by knowledgeable Wine Educators. Guests can enjoy tastings on the covered deck, inside the atmospheric barrel cellar, or in the exclusive Private Tasting Suite. Reservations are required for all visits.

As the founding vineyard on the North Fork of Long Island, Castello di Borghese honors its roots with authentic, old-world style wines. Since purchasing the vineyard in 1999, Ann Marie and Marco Borghese committed to growing exceptional grapes—a vision now carried forward by second-generation owner Giovanni Borghese.

With a small team and a big heart, they warmly welcome guests to experience their craft firsthand. Visitors are encouraged to bring a picnic, snap a selfie by the iconic mural, book a private tour, or host intimate events in their charming venue.

Croteaux Vineyards is the only vineyard in the U.S. exclusively dedicated to growing vinifera grapes for crafting rosé wines. Established in 2003, the vineyard, winery, and tasting garden sit amid two historic farms with agricultural roots dating back to the 1700s. Summer visitors enjoy sipping fresh vintages in a picturesque setting—each year’s rosés debut at the season’s start and sell out by fall.

For Claudia Purita, sustainability and self-reliance are more than principles—they’re a way of life. Raised on her family’s farm in Calabria, Italy, Claudia learned the value of the land early on, helping tend vegetables, grapes, and animals. After years in the restaurant industry on Long Island, she returned to her roots, hand-planting much of the vineyard and meticulously caring for every vine herself. Her dedication shines through in every bottle, offering a true taste of what one woman’s passion and hard work can achieve.

Founded in 1986 as a father-son collaboration, Jamesport Vineyard is one of the North Fork’s oldest and most beloved wineries. Housed in a renovated 165-year-old barn, the tasting room has expanded to welcome growing numbers of visitors. The spacious lawn hosts seasonal weekends filled with wine, light fare, and summer jazz concerts, while additional event spaces are perfect for weddings and private gatherings. With Ron Jr. continually updating vineyard plantings, Jamesport remains dedicated to producing some of the highest-quality fruit—and world-class wines—in the region.

Perched atop scenic bluffs overlooking the Long Island Sound, Kontokosta Winery invites guests to savor award-winning handcrafted wines grown in the region’s unique maritime climate. Family-owned and operated, the Kontokosta team is deeply involved in daily vineyard and farm management, ensuring sustainable practices that deliver consistent quality and ripeness vintage after vintage.

Established in 1980 by Kip and Susan Bedell—earning Kip the nickname “Mr. Merlot” from Wine Spectator—Bedell Cellars has become a benchmark winery on the East Coast. Now owned by the Lynne family, Bedell continues to lead with innovation, craftsmanship, and a deep commitment to producing world-class wines on the North Fork of Long Island.

Lieb Cellars is a 54-acre vineyard and full-service winemaking facility located on Long Island’s North Fork. Guests are invited to visit the laid-back tasting room to sample their small-batch wines or shop their full collection online.

Located in the hamlet of Cutchogue on the North Fork of Long Island, McCall Vineyards has been producing award-winning wines since 2007. Best known and loved for their exceptional Pinot Noir, McCall is dedicated to sustainable farming and crafting wines that reflect the character of the region.

Founded in 1983, Paumanok Vineyards is guided by a simple philosophy: exceptional wine begins with the healthiest, ripest grapes. Grown on 80 acres of estate vineyards, their wines include a range of varietals and blends—most notably New York’s only Chenin Blanc. Other offerings include Chardonnay, Riesling, Sauvignon Blanc, Cabernet Franc, Merlot, Cabernet Sauvignon, and Petit Verdot.