Kayak, Canoe, SUP Rental

Kayak, Canoe, SUP Rental

What Is The Kayak, Canoe, SUP Rental Trip?

Experience the Housatonic River between Great Barrington, MA and Sheffield, MA in one of our kayaks, canoes or stand-up paddleboards. This relaxing trip will allow plenty of time to enjoy the views of the Housatonic River Basin as you wind through the Housatonic River Valley for approximately three to four miles.

What will my day look like?

Check In 

After you make your reservation, and upon the time of your scheduled tour, you will meet our river shuttle and check in at the Upper Sheffield Covered Bridge, Covered Bridge Lane, Sheffield, MA 01257.

  • Waivers reviewed & signed at check in.

Gear Up & Pre-trip Orientation 

Once all guests have arrived at the meeting point in Sheffield, our shuttle will transport you to the put-in location up river in Great Barrington, MA.

Upon arrival at the put-in location, participants are equipped with:

  • PFD (personal flotation device)
  • Kayak, canoe or paddleboard
  • Paddle

Safety Briefing 

This is when we talk about the equipment you’re wearing, proper paddling technique, what happens if you fall into the river.


Prior to your put-in, our guides will ensure your equipment is fitting properly and demonstrate how to maneuver your craft through the water.

Paddle Down the River

Enjoy your Housatonic River experience. 


We will meet you at the end point in Sheffield where you will arrive just steps away from your vehicle.

Trip duration is approximately three hours, check-in to departure.

What to wear

Water appropriate footwear with heel straps are required. Quick-drying, non-cotton clothes are desirable. Please check our FAQs for more info on what to wear and what to bring with you.

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