Best Places to Kayak Near Windsor, MA

30 public launch points within 50 miles of Windsor, ranked by water conditions, access, and amenities.

30 nearby23 Lakes6 Rivers1 Reservoir
← All paddling in Massachusetts

Top Picks Near Windsor

a body of water surrounded by trees and bushes1

Ashmere Lake

Standout kayak fishing on the lake

LakeBeginner6 mi away
a large body of water surrounded by a forest2

Huntington

Calm, sheltered water that's ideal for beginners and paddle boarding

LakeBeginner19 mi away
a body of water with trees around it3

Cheshire Lake

Just 7 miles from Windsor — the closest quality launch

LakeBeginner7 mi away
boats on ground with dried leaves

Windsor Pond

Massachusetts · 4.1 mi

LakeKayakingCanoeingBeginner
a body of water surrounded by trees and bushes

Ashmere Lake

Massachusetts · 5.5 mi

LakeKayakingCanoeingBeginner
a body of water with trees around it

Cheshire Lake

Massachusetts · 6.9 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Cheshire Lake (Farnams Causeway)

Massachusetts · 7.2 mi

LakeKayakingCanoeingBeginner
boats on ground with dried leaves

Pontoosuc Lake

Massachusetts · 10.4 mi

LakeKayakingCanoeingBeginner
Kayakers on a calm forest river surrounded by pine trees

Housatonic River

Massachusetts · 11.5 mi

RiverKayakingCanoeingBeginner
green trees near body of water under blue sky during daytime

Onota Lake

Massachusetts · 12.3 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Windsor Lake

Massachusetts · 12.6 mi

LakeKayakingCanoeingBeginner
Kayakers on a calm forest river surrounded by pine trees

Housatonic River

Massachusetts · 12.8 mi

RiverKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Highland Lake (Lower)

Massachusetts · 13.2 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Highland Lake (Upper)

Massachusetts · 13.5 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Center Pond

Massachusetts · 14.8 mi

LakeKayakingCanoeingBeginner
A large body of water surrounded by trees

Richmond Pond

Massachusetts · 15.9 mi

LakeKayakingCanoeingBeginner
a body of water with trees around it

Laurel Lake

Massachusetts · 16.8 mi

LakeKayakingCanoeingBeginner
Kayakers on a calm forest river surrounded by pine trees

Hoosic River

Massachusetts · 17.3 mi

RiverKayakingCanoeingBeginner
a body of water with trees and houses in the background

Goose Pond

Massachusetts · 18.1 mi

LakeKayakingCanoeingBeginner
a body of water with trees and houses in the background

Shaw Pond

Massachusetts · 18.2 mi

LakeKayakingCanoeingBeginner
A large body of water surrounded by trees

Stockbridge Bowl

Massachusetts · 18.3 mi

LakeKayakingCanoeingBeginner
a large body of water surrounded by a forest

Huntington

Massachusetts · 18.7 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Cranberry Pond

Massachusetts · 20.4 mi

LakeKayakingCanoeingBeginner
a lake with trees around it

Lake Sadawga

Vermont · 21.0 mi

LakeKayakingCanoeingBeginner
Kayakers on a calm forest river surrounded by pine trees

Housatonic River

Massachusetts · 21.0 mi

RiverKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

South Stream

Vermont · 21.9 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Big Pond

Massachusetts · 22.8 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Upper Spectacle Pond

Massachusetts · 23.2 mi

LakeKayakingCanoeingBeginner
Kayakers on a peaceful lake surrounded by autumn foliage at sunset

Lake Garfield

Massachusetts · 23.6 mi

LakeKayakingCanoeingBeginner
Kayakers on a calm forest river surrounded by pine trees

Connecticut River

Massachusetts · 23.8 mi

RiverKayakingCanoeingBeginner
boats on ground with dried leaves

Benedict Pond

Massachusetts · 24.5 mi

LakeKayakingCanoeingBeginner
Kayakers on a calm forest river surrounded by pine trees

Connecticut River

Massachusetts · 24.6 mi

RiverKayakingCanoeingBeginner
a body of water surrounded by lush green trees

Otis Reservoir

Massachusetts · 25.2 mi

ReservoirKayakingCanoeingBeginner

Paddling Near Other Cities

Widen your search to towns within an hour of Windsor.

Savoy, MA5 miHinsdale, MA6 miDalton, MA6 miPlainfield, MA7 miCheshire, MA7 miBerkshire, MA7 miAdams, MA9 miCummington, MA9 mi

Frequently Asked Questions

What are the best places to kayak near Windsor, MA?

Top picks near Windsor include Ashmere Lake, Huntington, Cheshire Lake. In total there are 30 public launch points within 50 miles, with paddling on lakes, rivers, reservoirs.

What types of paddling can I do near Windsor?

Near Windsor you'll find opportunities for kayaking, canoeing, and stand-up paddle boarding. Most locations offer beginner-friendly conditions with public boat ramp access.

Are there free kayak launches near Windsor?

Yes! Most public boat ramps near Windsor are free to use. Some state parks and recreation areas may charge a small parking or entrance fee.