A Luxurious Wine Country Wedding at Kontokosta Winery
View of Vineyard and Tractor at Kontokosta Winery

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Greenport Holiday Guide

Valentine’s Day

Surprise your sweetheart this Valentine’s Day with a getaway in Greenport, where visitors can feel the love while indulging their taste buds at the many special events hosted by local businesses. Sparkling Pointe winery in Southold will offer a sparkling wine and cupcake pairing, while Pindar Vineyard in Peconic will celebrate with live music by Tommy Sullivan. For dinner, reserve a table for two at The Frisky Oyster or American Beech, both located in Greenport.

St. Patrick’s Day

This year, St. Patrick’s Day falls on a Saturday, making it the perfect opportunity to tour the craft breweries found on Long Island’s North Fork. Stop by the tasting room at Greenport Harbor Brewing Company, located just minutes from The Harborfront Inn, or see what’s on tap at Jamesport Farm Brewery, which serves “farm-to-pint brews” in Riverhead. You can also grab a seat at the bar at Brix & Rye, The Whiskey Wind Tavern, or any number of other nearby nightlife destinations.


Enjoy an abundance of family-friendly activities—and the first days of spring—during Easter weekend in Greenport. Before brunch, head to the Long Island Aquarium for the Penguin Egg Hunt (included with admission) or check out the Greenport Children’s Egg Roll in Mitchell Park. Whether you’re visiting relatives or simply enjoying a holiday getaway, The Harborfront Inn is an excellent choice for discovering the most festive events on the North Fork.