Located on Long Island’s bucolic 30-mile North Fork peninsula, Greenport is a charming seaside town with historic architecture, hip restaurants, and a thriving beer, wine, and spirits scene. It attracts weekenders seeking a more casual alternative to the ritzy Hamptons across the bay, and it’s renowned as a destination for wine lovers, boasting over 60 unique vineyards. Of those, Greenport is home to Kontokosta, serving both spectacular views and viognier. One Woman Wines, run by Italian expat Claudia Purita, has a tasting room in nearby Southold and is poured at Greenport’s First & South, a farm-to-table restaurant where the beverages are as locally sourced as the food. Equally popular are the many craft breweries and small batch distilleries nearby; beer drinkers hop to the tasting room at Greenport Harbor Brewing Co. for an IPA flight, while cocktail aficionados pick up spiced rum, vodkas, and grappa from Greenport Distilling. The hotel scene has also boomed, with three openings this season alone including Hotel Moraine, Silver Sands, and ZEY Hotel, owned by restaurateur and reality TV star, Zach Erdem.

 

In order to qualify as one of America’s Best Small Towns, a town must be located in the United States and have a full-time population below 25,000 residents, according to the most recent U.S. Census Bureau data. It must also excel in its category and and offer a variety of activities, accommodations, and a timely reason to visit — be it a notable new festival, hotel, restaurant, attraction, or tourism initiative. 

 

They polled their colleagues and contributors, trusted travel advisors, and more within their network of experts from all over the U.S. Their team of travel editors then sifted through the many thoughtful responses and chose the destinations they believe readers will enjoy the most right now.

 

America’s Best Small Beach Town

Winner: Boca Grande, Gasparilla Island, FL

Runner-up: Port Aransas, Texas

 

America’s Best Small Mountain Town

Winner: Highlands, NC

Runner-up: Red Lodge, MT

 

America’s Best Small Lake Town

Winner: Grand Marais, MN

Runner-up: Wolfeboro, NH

 

America’s Best Small Desert Town

Winner: Kanab, UT

Runner-up: Yucca Valley, CA

 

America’s Best Small Food + Culture Town

Winner: Los Olivos, CA

Runner-up: McCook, NE

 

America’s Best Small Wine, Beer + Spirits Town

Winner: Dahlonega, GA

Runner-up: Greenport, NY

 

America’s Best Small Spa + Wellness Town

Winner: Aurora, NY

Runner-up: Girdwood, AK