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Chesapeake Description

The Chesapeake is a kayak brought to you by Wilderness Systems. Read Chesapeake reviews or submit your own review to share with the paddling community. Check out a few other kayak recommendations below or explore all kayaks to find the perfect one for you!

Wilderness Systems
Chesapeake Reviews

Read reviews for the Chesapeake by Wilderness Systems as submitted by your fellow paddlers. All of the reviews are created and written by paddlers like you, so be sure to submit your own review and be part of the community!

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I was gifted a 1995…

Submitted by: paddler1721777 on 9/13/2021

I was gifted a 1995 Chesapeake by my brother 2 yrs ago. He had it for several years before he bought a solo canoe just because it was lighter. It is built out of fiberglass and weighs in the low 30 lbs. range. It's very stable even in white caps. Best kayak I've ever owned & I've had several. Made custom yoke for it for portaging. Seating in it wasn't the best so I removed it cause of lack of comfort & weight. Has a few dings and even fell of trailer at 50 mph and you can't tell(brothers fault oops). Love it so much thinking about getting buried in it! Awesome kayak!


I have owned my Wilderness…

Submitted by: paddler236840 on 6/6/2016
I have owned my Wilderness System Chesapeake model for over 15 years now. I have the Kevlar and glass version and have put it through the wringer( one must remember the washing machines of the fifties to relate to what put through the wringer means ) and only have one "ding" to show for the effort. This watercraft is tough, forgiving for the newbies, and looks like new some 15 years after purchase. Everyone loves the comfortable cockpit and ease of paddling. I paid a lot less than you're going to pay now but YOU will get your monies worth with proper care. That just means wash it off after every trip and store it out of direct sunlight. This kayak is a "10" for fly fishing or touring on inland river systems.I love mine and at 66 years of age it would be hard to sell me on any other kayak.

The Chesapeake by Wilderness…

Submitted by: paddler236440 on 8/19/2015
The Chesapeake by Wilderness Systems is a great kayak. It's light weight and easy to handle, very stable, easy paddling, and tracks well. There's plenty of storage and the large cockpit is easy to get in and out of. In addition to lots of fun for play, it's great for fishing. You can add a pole bracket if you want and catch while just paddling around. There's enough space in the cockpit to put a large bucket for the fish. The Chesapeake works well in ponds, lakes, bays and coastal oceans. In open ocean, it's a little short for breaking the crests smoothly so it's up and down and it can be a slow tiring progress. The Chesapeake is rugged. I've had mine for many years, never needed repairs and it still looks very good.
Overall, it's a great kayak and yes, I did sell my canoe!

This yak is great. I use it…

Submitted by: troutstalker on 8/9/2013
This yak is great. I use it on wilderness trips in the Adirondacks. I built a yoke for portaging from pond to pond. I modified it by removing the seat so I could slide my backpack under the rear deck. I added a lighter stadium seat which I remove at campsites to sit on.

This yak is great in streams, rivers and open water. I have paddled in windy conditions and it handles great! My only regret is they don't build them anymore!


I own two of these boats in…

Submitted by: paddler231522 on 4/17/2006
I own two of these boats in fiberglass, one for my wife and one for myself, and love them both. I have taught many non paddles the basics in a very short time and they have enjoyed themselves quickly. Even my 12 year old grandson mastered the basics quickly and enjoyed going on lakes with me. Tracks wonderfully, very stable and user friendly.

At age 65, features of…

Submitted by: guest-paddler on 10/6/2003
At age 65, features of lightweight Kevlar and ease of entering and exiting via the large cockpit were very appealing. I have been thoroughly enjoying the Chesapeake Pro several times a week for the last seven months on local lakes, ponds and primarily the Connecticut river in Massachusetts. This is a terrific performing, well designed and user friendly craft. I am ready to sell the canoe.

I bought the Kevlar version.…

Submitted by: guest-paddler on 5/7/2001
I bought the Kevlar version. It is very light weight and is easily loaded on top of the car by one person. I use mine for fishing and it works great. It is very maneuverable and requires little effort to paddle. Not a good boat for rough water. Because the cockpit is so large you pick up alot of paddle drip. I bought a half skirt which eliminated the problem. It also works great as a shelf for fishing tackle and keeps your legs out of the weather.

Lightweight fiberglass boat…

Submitted by: paddler229086 on 1/29/2001
Lightweight fiberglass boat with large cockpit and opening. Very stable and good for beginner or intermediate. The boat is wonderful in lakes and fairly calm bays - it's fast, glides and tracks well. I don't think it would be terrific for open ocean, too short. it weighs 36 pounds and really easy for one person to handle. I get it on top of a van with no problem. The only complaint is the nature of a fiberglass boat, they're brittle and prone to scratch - but if you're careful in the water it's great.