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Guide to NYC Places to Go

Don’t Wait Until Labor Day to Plan Your Long Weekend

August 21, 2019

As a busy, hard-working New Yorker, you deserve a vacation. You deserve one whenever the opportunity arises, whether it’s that long-planned-for week in Hawaii or the next long weekend; whether it’s a few days off to celebrate your anniversary or birthday or just one day at home. Work and ambition aside, life truly is about spending quality time with those you love. Thankfully, another three-day weekend is upon us, as Monday, September 2 is Labor Day. According to the US Department of Labor, Labor Day “is a creation of the labor movement and is dedicated to the social and economic achievements of American workers.” Celebrate your achievements. Make more memories with loved ones. Here are a few ideas…

The Catskills

A weekend in the Catskills is always a good idea. Catskill towns are beautiful, artsy, invigorating, and alive with creative energy. They’re the perfect mix of nature and culture. They’re graced with both lush forests, crystal clear swimming spots, and quaint inns with stunning views, as well as hip cafes and wine bars, local shopping, and music and art festivals. This year is particularly special in the Catskills, as it’s the 50th anniversary of Woodstock. Head to Bethel Woods Center for the Arts to check out the many commemorative activities happening at the original site of the iconic festival. Give a boost to your own health and mindfulness this Labor Day weekend at the Mind: Body: Earth festival, or get your fix of artisanal crafts, live music, and alpacas at the Harvest Festival. Only a two-and-a-half-hour drive gets you from the heart of Midtown to the heart of the Catskills for a Labor Day weekend filled with music, art, and nature. 


If a beach scene is more your thing, why not head to the most quintessential of beaches: Bermuda. It may seem like a stretch. But, the reality is, Bermuda is only a two and a half hour flight from JFK. And, yes, Bermuda beaches might be slightly more crowded on Labor Day weekend because most islanders are off work and celebrating. But that’s the case with beaches everywhere during Labor Day. And, while it’s true that many shops and restaurants will be closed, and that public transit will be limited, there are still many fun and interesting things to do in Bermuda on Labor Day. All public beaches are open, as is the Bermuda Aquarium, Crystal & Fantasy Caves at Bailey’s Bay, Bermuda Underwater Exploration Institute, and the Gibbs Hill Lighthouse, to name just a few. If you like a little history and fun-spirited activism to go with your Labor Day, the Bermuda Industrial Union sponsors speeches, festivities, road races, and games on this day. But, the best part of a Bermuda vacation for Labor Day weekend: the water temperature at Bermuda’s pink sand and aqua colored beaches is still 81 degrees.

The Berkshires

From Brooklyn to the Berkshires is about a four-hour drive, and Ben Harper is playing at Tanglewood the weekend of Labor Day. It’s a glorious mouthful, but a legitimate excuse to get up there. Beautiful year-round, Lenox, Massachussettes boasts nature, culture, places of historical relevance, and Tanglewood—the world-famous music center and summer home to the Boston Symphony Orchestra. On Labor Day weekend alone, Tanglewood is hosting Melissa Etheridge and Pat Benatar, Ben Harper and Trombone Shorty, and Reba McEntire. Take your pick or pick them all. While you’re there, grab your boots and head off to the 50 miles of hiking trails which lead to the state’s highest peak, Mt. Greylock. You can even sleep and eat at the top, where there’s a rustic 1930’s lodge constructed by the Civilian Conservation Corps. Or take advantage of the Arcadian Shop, which will deliver kayaks to you and then pick you up after a few hours of paddling on the Housatonic, the winding water walkway that twists itself around the Berkshires. Take a tour—maybe even the popular Ghost Tour—of The Mount, Edith Wharton’s historic home; or just enjoy the renowned restaurants of Lenox, which is at the center of the locally-grown food movement. Whatever you do in the Berkshires, the beauty of its nature and the quality of its culture is enough to rejuvenate you until your next three-day vacation.  

White Water Rafting

It’s true: it’s only a three-day weekend. You might be the type who wants to pack in as much fun, excitement, and adrenaline-producing action as you can. The great news is that you can leave Manhattan in the morning, go white water rafting for hours, and be back on the Upper West Side by dinner. With Discover Outdoors and The North Face, you don’t even have to drive—they shuttle you there and shuttle you back. These trips are beautiful and thrilling, but appropriate for even first-time rafters. And when someone asks you what you did for Labor Day and you tell them you went whitewater rafting, you’ll sound adventurous and exotic—even in New York.

Feel like just hanging out at a beach near home this Labor Day weekend? That, too, is a solid plan. Here’s a list of nearby beaches for fun, sun, and Labor Day relaxation.

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