Hudson Valley Weekend Getaway To Beacon, NY | Tasting Table NYC

Let your freak flag fly on a Beacon summer Friday

Frank Billingsley sits outside the Beacon Creamery, the ice cream parlor where he works at the western end of Beacon's curving Main Street, gently strumming a banjo whilst wearing a Hawaiian-esque floral-print shirt and straw fedora.

He smiles at passersby. If a kid likes the music, he chats them up and lets them hold the banjo.

Folks like Billingsley and the "you-do-you, anything goes" mindset are what make this small Hudson Valley town, located about an hour and a half north of the city by car, special and lovely and weird. Sure, there's been a fair influx of bougie elements, but the gallery-dotted Main Street retains its freewheeling artsy spirit. Speaking of art: The gorgeous contemporary Dia:Beacon museum, located just down the hill, is a worthy destination in its own right.

The east end of Main Street | Lobster roll at The Roundhouse | Frank Billingsley | Paté at The Hop

But let's stick with Main Street for now. Stroll past its murals and old-fashioned Car Wash signs and you'll pass a no-frills ribs-and-fried chicken joint called BJ's Restaurant, barber shops and a mirror-lined diner from 1946, New Age-y massage joints, vintage clothing and antique shops, and well-curated boutiques selling luxurious bath products and market totes. (See the slideshow for our favorite spots.)

Beacon is kind of the perfect city escape: It's easy to get to (hello, Metro-North station), it's real pretty—what with its low brick buildings and surrounding lush green hills—and it's got good food and drink. And everyone, from restaurant servers to chatty residents, is smiley. It may take a little getting used to, but try it, you'll like it.

"It's pretty quiet up here, but all you Brooklyn people keep moving here," Steve Astorino, owner of the Zora Dora paleta shop, jokes with me when I drop by for a popsicle.

As I recalled the past few hours of relaxing, out-of-the-city bliss and took my first very cold bite of fragrant lavender-honey paleta, I thought to myself, "That might be a very good idea someday."