Keepin’ It Cool: Hammondsport takes America’s Coolest Small Town title to heart

Blogger Will McGough took the Coolest Road Trip to the four East Coast towns in Budget Travel's Top 10 Coolest Small Towns list.

As soon as you turn onto Route 54A in Hammondsport, passing by quaint homes and charming B&Bs – a pristine lake in the background – you know you’re somewhere special. It becomes more apparent the closer you get to the Village Square. When you see the banner welcoming you to “America’s Coolest Small Town,” it all makes perfect sense. Even before you step out of your car, you sense the title fits the town like a glove. There’s a distinct cool factor that encapsulates a town built around “Wings, Wine and Water” – and it begs to be discovered and enjoyed.

How it happened

Nestled at the head of “Y-shaped” Keuka Lake, Hammondsport is home to about 725 residents, and sees tens of thousands of tourists each year.

In January – a time of year when few flock to a lakeside community in Upstate New York – Hammondsport was able to rally supporters to help vote it as “America’s Coolest Small Town” in the annual Budget Travel magazine competition, garnering more than 130,000 votes. Supporters could cast a vote once every 24 hours.

On January 31, the final day of competition, voters overwhelmed Budget Travel’s servers, causing the site to crash. Magazine editors did what they believed was the only fair thing, and called a tie between the top two towns, which were separated by just fractions of a percent. Hammonds-
port shares its victory with Beaufort, North Carolina, a beach town in the Southern Outer Banks.

A cause for celebration

Not a moment after the tie was announced, Hammondsport kicked into celebration mode. The town swarmed with local media, and residents swelled with hometown pride.

In the weeks following the announcement, the town worked relentlessly to maintain the buzz surrounding the contest. The first thing officials decided was needed was a new logo to represent Hammondsport’s cool aspects. With that, the Hammondsport Chamber of Commerce initiated yet another competition. Nearly 20 entries and a tough decision later, they implemented the winning design into all things related to Coolest Small Town. Restaurants made banners displaying it proudly. Wineries hung signs bearing the emblem. And everything from T-shirts to coffee mugs and Christmas ornaments went on sale.

But this still wasn’t enough. Hammondsport needed to say thank you.

“When the voting was taking place it wasn’t confined to just residents and businesses in Hammondsport,” said Brett Steeves, president of the Hammondsport Chamber of Commerce. “In fact, boundaries usually marked by townships and county lines, even state lines, all but disappeared. In recognition of that fact, Hammondsport hosted this event as a way to reach out to the surrounding region and show our appreciation.”

On June 30, the Hammondsport: Coolest Small Town Celebration drew hundreds of supporters to the Village Square. The event featured everything from a NASCAR race car to alpacas, but the big draw was Taste of the Coolest Small Town: Finger Lakes Wine and Beer. Celebration goers purchased their collectible wine glass, bearing the new logo, and tasted the flavors for which Hammondsport is famous. The celebration ended with a seaplane flyover and the Fireman’s Parade and Carnival.

“This title has put Hammondsport in a very public spotlight this year,” said Peggy Coleman, president of the Steuben County Conference & Visitors Bureau (CVB). “We were excited to celebrate in this special way with the people who made it all possible.”

Coolest Road Trip blogger searches for the cool factor

And yet, Hammondsport wanted to do more. As the official tourism marketing agency for the county, the Steuben County CVB came up with an idea to send a travel writer to the four cool East Coast towns in Budget Travel’s top ten. Blogger Will McGough of agreed to make the 13-day road trip (in an extremely decked-out car) to Cape May, New Jersey; Beaufort, North Carolina; Damascus, Virginia; and finally, Hammondsport. He spent, on average, two to three days in each town with one goal in mind: to seek out whatever it is that makes it so cool.

“Hammondsport seems like the perfect blend of the other three towns,” McGough commented, as he sat on the deck of Bully Hill Restaurant, overlooking sparkling Keuka Lake. He had only been in Hammondsport for a few hours, and already, he was captivated by the beauty, tranquility and – yes – the undeniable cool factor he could sense in the area.

McGough was in Hammondsport from June 29 through July 1, ending his long trip with lots of wine tasting, a scenic flight over the Finger Lakes, jet skiing on Keuka Lake and a hot-air balloon ride – all things people can do when they visit – over America’s Coolest Small Town.

“In addition to arriving on the first of two holiday weekends, the town was also celebrating their recog-
nition as the Coolest Small Town in America with a parade and festival in the downtown square,” McGough said in a blog post. “Something about the people’s passion and excitement has really stuck with me, seeing them so proud of where they live.

“While big cities often draw residents solely because of industry and opportunity, it’s rare that someone ends up in a small town like Hammondsport (or Beaufort or Cape May or Damascus) for any other reason than love of the area. They all really want to be there, which makes me even more curious to find out why, both as a person and a travel writer.”

To read McGough’s blogs about Hammondsport, visit
The deputy editor of Budget Travel magazine, Marc Peyser, also visited Hammondsport in June. Make sure to check out his article in the September/October issue, currently available on newsstands.

For information to plan your trip to America’s Coolest Small Town, please visit

by Kimberly Price Thompson

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