View Current Travel Advisories
Trailways Home Page

Trailways Bus Tickets
from Pickering, ON to Sheffield, MA

(*) indicates a required field
Start typing the origin city to open location options, and then use the arrow keys to navigate to the origin city you want, then press enter to select that origin city
Start typing the destination city to open location options, and then use the arrow keys to navigate to the destination city you want, then press enter to select that destination city

Travel made simple with Trailways

Unbeatable Prices

One of the best inventories of bus tickets in one place - with exclusive fares you won't find elsewhere.

Proven Reliability

On-time travel services - trust our reputation for reliable bus transportation.

Comfort and Convenience

Numerous upgraded buses with large leather recliners, free wi-fi, and power outlets for each seat.

Bus Station Information for Sheffield, MA

Sheffield (Depot Square)

Flag Stop, use arrow keys or tab to explore more about this bus station

Sheffield, MA 01257

Flag Stop
Address
107 Main Street 
Sheffield, MA 01257
Phone Number
(800) 343-9999/(800) 858-8555
More Detailsabout Sheffield (Depot Square) Flag Stop

City InformationforPickering, ON

Ready for a delightful escape? Hop on a bus to Pickering, ON, where small-town charm meets lakeside beauty. This Ontario gem offers an inviting mix of nature, history, and leisure activities perfect for any traveler.

Start your journey with a visit to the Pickering Village Museum, where you can wander through a living history experience depicting 19th-century rural life. Next, head to Frenchman’s Bay for a refreshing stroll along the waterfront, where sailboats dot the horizon and the air is crisp with the scent of nature.

If you’re into trails, the Seaton Hiking Trail is a must, meandering through lush forests and scenic views that invigorate the soul. Ready to dive into local culture? Check out the thriving arts scene or pop by café-lined streets for a friendly chat with locals.

Whether you’re looking to unwind by the bay or explore the town's charming streets, Pickering has something for everyone. So grab your tickets, settle into your seat, and let your bus to Pickering open the doors to easygoing adventures and friendly faces.

City InformationforSheffield, MA

Nestled in the heart of the Berkshires, Sheffield, MA, is a welcoming town brimming with rustic charm and natural beauty, making it a perfect retreat for travelers. As you step off your bus to Sheffield, MA, the town offers a blend of quaint allure and exciting outdoor adventures. Embrace the serene landscapes of Bartholomew’s Cobble, a National Natural Landmark, where richly biodiverse trails promise an invigorating hike. The town is also known for its lively arts community, so snagging a piece of local art to take home might just be in the cards.

For those with an appetite for history, a visit to the Sheffield Historical Society, complete with fascinating exhibits, sheds light on the area's storied past. Dive deeper into the local flavor with a meal at an eatery serving farm-fresh bounty—this town thrives on its dedication to community and sustainability.

Whether you’re in search of nature’s tranquility or a cultural infusion, Sheffield rolls out the welcome mat. Secure your seat on the next bus to Sheffield to explore everything this charming town has to offer!

Frequently Asked Questions about the Bus Ride

Discover our Most Popular Routes Nationwide