
Buses from Stroudsburg, PA to Chestertown, NY travel the 312mi (502.11km) journey, taking approximately 8h, 40m. Usually, there are 18 buses operating per day. While the average ticket price for this journey is around $121.13, you can find the cheapest bus tickets for as low as $118.31.
Chestertown, NY 12817
Feel like stepping into America’s quaint charm on your next journey? Hop on a bus to Stroudsburg, PA, and uncover this delightful town nestled in the heart of the Pocono Mountains. With its rich blend of natural beauty and small-town warmth, Stroudsburg welcomes travelers seeking a memorable escape.
Start your exploration at the Sherman Theater, famous for live performances ranging from local talents to big-name acts. Art lovers will appreciate the town’s creative streak at the Andrei Art Gallery, featuring works from both regional and international artists. For a walk on the wild side, the nearby Delaware Water Gap offers hiking trails with breathtaking views and outdoor adventures for every skill level.
As you wander downtown, you’ll find boutique shops and cozy cafés that make Stroudsburg’s streets feel like a home away from home. Foodies, your taste buds are in for a treat with a variety of delicious dining options, from American classics to international delights. So buckle up and let the Trailways bus ride lead you to the charms of Stroudsburg, PA. Your next adventure is just a ticket away!

Take the scenic route and hop on a bus to Chestertown, NY, where rustic charm meets the serenity of the Adirondacks. Nestled amidst snow-kissed peaks and whispering pines, this quaint town is your ticket to nature-filled adventures and cozy, small-town delights.
Start by embracing the outdoors, hike up Panther Mountain for panoramic views that promise to take your breath away. If water calls your name, spend a lazy afternoon kayaking on the crystal-clear waters of Friends Lake.
Back in town, the local vibe is pure magic. Stroll through Main Street’s eclectic mix of shops, where each corner tells a story, and your taste buds will thank you after sampling homemade goodies at the local bakeries.
Music lovers will be enchanted by the Chestertown Summer Concerts series, where local talent sets the perfect soundtrack to your evening under the stars.
So, what are you waiting for? Pack your bags and book that bus to Chestertown, the town that every traveler wishes they’d discovered sooner.
How long does it take to get from Stroudsburg to Chestertown?
How many buses are there from Stroudsburg to Chestertown?
How early should I arrive at Stroudsburg?
What is the average cost of the trip?
What bus companies offer services?
How long does it take?
What if my question isn't listed?