Length: 50 miles

Towns: Portland, East Hampton, Glastonbury, Manchester, Bolton, Vernon, Tolland, Ellington, Somers, Stafford

Trail Overview: The Shenipsit Trail system extends from the Cobalt area of East Hampton north to just shy of the Massachusetts border in West Stafford. The trail traverses the Meshomasic and Shenipsit State Forests on trails that are primarily woodland paths and offer several outstanding views. The Shenipsit also connects to the trail systems in Gay City State Park in Hebron, Case Mountain Recreation Area in Manchester, and Valley Falls Park in Vernon. Points of interest along the Shenipsit Trail include spectacular views of Great Hill Pond and the Connecticut River, excellent views of Hartford from the summit of Case Mountain, a junction with the Hop River Rail Trail in Bolton, scenic sections on the banks of the Tankerhoosen River in the Belding and Tankerhoosen Wildlife Management Areas in Vernon, and excellent views to the west, north, and southwest from the fire tower on Soapstone Mountain in Somers. The trail also crosses conservation lands protected by the Kongscut Land Trust and the Manchester Land Trust.

Allowed Uses: Hiking, Biking (only in specific areas)

Partners: Connecticut Department of Energy & Environmental Protection (CT DEEP), Kongscut Land Trust, Manchester Land Trust, Tolland County Agricultural Center, Meshomasic Hiking Club, Shenipsit Striders, Town of Vernon, Town of Glastonbury
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Trails

titleriding arearatingdistancecompleted
1Windham Road
Meshomasic State Forest - Diamond Lake Block
774 ft
2Shenipsit Trail - Charter Oak Greenway Rt 85 Loop
Bolton
574 ft
3Valley Falls Loop Trail West
Valley Falls
3,684 ft
4Shenipsit Trail
Meshomasic State Forest - Mountain Block
5 miles
5Shenipsit Trail
Meshomasic State Forest - Mountain Block
3 miles
6Shenipsit Trail
Meshomasic State Forest - Diamond Lake Block
3 miles
7Old New London Turnpike
Meshomasic State Forest - Diamond Lake Block
4,311 ft
8Portland Reservoir Road
Meshomasic State Forest - Mountain Block
5,128 ft
9Kongscut Garnet Trail
Case Mountain
1 mile
10Carriage Path
Case Mountain
3 miles
11Shenipsit Trail
Meshomasic State Forest - Diamond Lake Block
2 miles
12Shenipsit Trail - Bolton Center Road
Bolton
430 ft
13Shenipsit Trail - Commuter Lot Path
Bolton
141 ft
14Reservoir Road
Vernon
4,262 ft
15Sodom Road
Shenipsit State Forest
2,264 ft
16Shenipsit-Gay City Connector & Outer Loop
Gay City State Park
2,126 ft
17Shenipsit Gay City Connector no bicycles
Gay City State Park
3,645 ft
18Shenipsit Trail - Charter Oak Greenway
Manchester
4,249 ft
19Shenipsit Trail (Blue Blaze)
Case Mountain
4 miles
20The Highland Trail
Case Mountain
276 ft
21Charter Oak Greenway Notch loop
Bolton
554 ft
22Birch Mountain Trail (Blue/Yellow Blaze)
Case Mountain
4,534 ft
23Shenipsit Trail
Bolton Notch
889 ft
24Dickenson Road
Glastonbury
2,156 ft
25Mott Hill Road
Glastonbury
4,698 ft
26Country Club Road
Glastonbury
2,595 ft
27Wassuc Road
Glastonbury
1,437 ft
28Toll Gate Road
Glastonbury
3,757 ft
29Cascade Spur
Glastonbury
226 ft
30Pheasant Crossing
Glastonbury
226 ft
31Shenipsit Trail
Glastonbury
728 ft
32Hebron Avenue (Rt 94)
Glastonbury
289 ft
33Birch Mountain Road
Glastonbury
1,509 ft
34Shenipsit Access.
Case Mountain
2,162 ft
35Shenipsit Gay City Connector no bicycles
Gay City State Park
2,740 ft
36Outer Loop Trail (North)
Gay City State Park
1,877 ft
37Outer Loop Trail (North)
Gay City State Park
4,186 ft
38Outer Loop Trail / Pond Loop
Gay City State Park
1,394 ft
39Outer Loop Trail (South)
Gay City State Park
2 miles
40Connector Trail
Gay City State Park
4,108 ft
41Pond Loop Trail
Gay City State Park
2 miles
42Pond Loop Trail (south)
Gay City State Park
2,805 ft
43Pond Loop Trail (Beach)
Gay City State Park
748 ft
44Split Rock Trail
Gay City State Park
2,021 ft
45Orange Connector
Gay City State Park
1,358 ft
46The Lookout Mountain Trail (Yellow Blaze)
Case Mountain
4,829 ft
47Shenipsit Trail
Bolton Notch
1,919 ft
48Hop River & Shenipsit Trails
Bolton
2 miles
49Risley Loop
Risley Park
2 miles
50Valley Falls Loop Trail East
Valley Falls
1 mile
51Shenipsit Trail
Valley Falls
3 miles
52Belding WMA
Valley Falls
2,178 ft
53Hartford Turnpike
Vernon
837 ft
54Shenipsit Trail Tolland Ag Center
Vernon
3,369 ft
55Gerber Drive
Vernon
725 ft
56Industrial Park Road East
Vernon
1,296 ft
57Hartford Turnpike
Vernon
738 ft
58Kingsbury Avenue
Vernon
2,470 ft
59Tolland Avenue
Vernon
1,033 ft
60Shenipsit Trail
Tolland
2 miles
61Shenipsit Lake Road
Tolland
2 miles
62Grahaber Road
Tolland
2,612 ft
63Shenipsit Trail
Tolland
1 mile
64Crystal Lake Road
Ellington
440 ft
65Hopkins Road
Ellington
627 ft
66Shenipsit Trail
Shenipsit State Forest
5 miles
67Sodom Road
Shenipsit State Forest
751 ft
68Shenipsit Trail
Shenipsit State Forest
4,836 ft
69Chestnut Hill Road (RT 190)
Somers
348 ft
70Galbraith Road
Somers
1,099 ft
71Avery Road
Shenipsit State Forest
420 ft
72Shenipsit Trail
Shenipsit State Forest
3,888 ft
73Country Road
Shenipsit State Forest
118 ft
74Shenipsit Trail
Shenipsit State Forest
2 miles
75Old Springfield Road
Somers
52 ft
76Greaves Road
Somers
673 ft
Displaying 76

Videos

youtuber WHATS MY CONNECTICUT MOUNTAIN BIKING FAMILY...
20:28 | 407 | Feb 20, 2021 , Manchester

Recent Trail Reports

statustraildatecondition
Shenipsit Trail
Jun 21, 2026 @ 11:51am (America/New_York)
Jun 21, 2026
view
Hop River & Shenipsit Trails
Jun 21, 2026 @ 11:51am (America/New_York)
Jun 21, 2026
view
Birch Mountain Trail (Blue/Yellow Blaze)
May 11, 2026 @ 5:22pm (America/New_York)
May 11, 2026
view
Shenipsit Trail
Apr 9, 2025 @ 4:59pm
Apr 9, 2025
view
Avery Road
Apr 9, 2025 @ 4:59pm
Apr 9, 2025
view
more reports »
Total Trails
76
Total Distance
66 miles
Total Descent
-7,120 ft
Total Climb
7,274 ft
no votes yet
56 |
Feb 16, 2026 @ 12:06pm
Feb 16, 2026
66 |
Feb 16, 2026 @ 10:56am
Feb 16, 2026
36 |
Jan 15, 2026 @ 6:14am
Jan 15, 2026
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