Five Unforgettable Weekend Motorcycle Trips from Brooklyn

For city riders like us, Brooklyn’s skyline can start to feel like a cage. Luckily, the Northeast is stitched together with some of the best two-lane roads, mountain switchbacks, and river routes you’ll find anywhere. Here are my top five weekend trips for riders who know the value of trading traffic lights for winding roads.

1. Adirondack Mountains: Peaks, Pints, and Olympic History

If you want a big ride that combines scenic parkways, lakeside roads, and mountain air, point your front wheel toward Lake Placid. Kick off on the Taconic State Parkway—keep your eyes open for deer—and make your first overnight in Saratoga Springs, where history and craft beer come together. The next day, push deeper into the Adirondacks, tracing Route 9N past Lake George toward the Olympic Ski Jumping Complex. Big Slide Brewery offers a cold pint after a day in the saddle. On the final day, carve your way south through Saranac Lake and Glens Falls before the interstate hums you back to Brooklyn.

Ride Tips: Fuel is sparse, weather’s unpredictable—check your brakes, pack rain gear, and top off the tank when you can

.

2. Catskill Mountains: Woodstock’s Free Spirit on Two Wheels

A shorter hop, but one full of soul. The Catskills ride is all about winding roads and cultural stops. Route 28 is your ticket to Woodstock, with Kingston and Phoenicia as tasty pit stops. In town, walk through the Woodstock Artists Association & Museum or hike Overlook Mountain for sweeping Hudson Valley views. Fuel up with craft brews and farm-to-table bites before looping back to the city through New Paltz—don’t miss brunch at Main Street Bistro

.

Ride Tips: Watch for rain showers and sharp curves—these backroads twist and test you in the best way.

3. Hudson Valley: River Roads and Historic Hideaways

If you crave river views and history, this ride is for you. From Brooklyn, roll up the Palisades Interstate Parkway, hugging the Hudson River’s western bank. Take Route 9W north, cutting through Nyack and Newburgh to Hudson, NY. Drop your kickstand at the Olana State Historic Site, grab a pint at Hudson Brewing, and soak up the local farmers market. Swing through Bear Mountain State Park on the way back—stretch your legs on a quick hike before lunch at The Filling Station

.

Ride Tips: Bring a GPS or offline map—these rural roads can get twisty fast.

4. The Poconos: Pennsylvania’s Winding Backroads

Head southwest through the Delaware Water Gap and into Pennsylvania’s Poconos, ending up in Jim Thorpe—a gem of Victorian history and charm. Take Route 611 for a satisfying sweep of curves through Stroudsburg and Mount Pocono. Once there, park the bike and hop the Lehigh Gorge Scenic Railway or tour the Asa Packer Mansion. End the day with steak and beer at Molly Maguires before sleeping off the miles at The Inn at Jim Thorpe

.

Ride Tips: Start early to dodge city traffic. The mountains can surprise you with sudden weather changes—dress smart.

5. Vermont’s Green Mountains: Winding Byways and Craft Beer

When you’re hungry for real miles, ride north into the Green Mountains. This ride loops through the Berkshires to Bennington, then up Route 100—arguably one of the finest motorcycle roads in New England. From the Bennington Battle Monument to the Vermont Marble Museum in Proctor, every stop adds a layer of local flavor. Stay at Killington Grand Resort and plot your leisurely route home through Woodstock, Cold Spring, and the Hudson Valley

.

Ride Tips: Vermont is gorgeous but remote—download maps, top off your tank, and plan around weekend festival traffic.

Final Thoughts

Every road out of Brooklyn holds the promise of a new story. So prep your bike, pack light, and ride far. These five weekend escapes aren’t just about distance—they’re about finding something worth the miles.

See you out there.