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SaveBennett's Pond is part of the Connecticut State Park System. Together with Ridgefield's Hemlock Hills, Pine Mountain and Lake Windwing [Ridgefield Open Space Association (ROSA)] it forms one of the largest nature preserves in the Southwest portion of the state. Glacial activity has left numerous erratic boulders and small cliffs throughout the area. Featuring a wide variety of terrain it's a picturesque place and any ride here is bound to be memorable.
The area consists of meadows, woodlands, wetlands and steep ridges all traversed by great trails of varying difficulty. The ride down to the pond is an easy and fast downhill but as you go north into Pine Mountain or further west into Hemlock Hills, the terrain can be challenging.
Trails feature twisty tight single track along rock-strewn ridges; there's even a massive slick rock section. With some hike a bike in the northern reaches—Bennetts is still a diamond in the rough but an awesome park to explore.
Fore more information go to the Fairfield Couty NEMBA website.
Update 9/20/20
NW CT NEMBA completed our final major trail project in Hemlock Hills in Ridgefield CT. Hemlock Hills/Pine Mtn/Bennett’s Pond is among the largest contiguous open spaces in Fairfield County and has become very popular. FCNEMBA has been working for many years with the Ridgefield Conservation Commission (RCC) on various trail projects, and this summer we legitimized the last of the old “social” trails. We built several reroutes to reduce erosion, and closed some “pop-up” trails to reduce proliferation and help the RCC achieve the natural aesthetic that is a foundation of their policy.
Our maps guru, Rich Coffey, has been focused on getting our trail systems updated on Trailforks. Most of our open spaces have cell-service and having updated GPS maps has been very helpful for our new members. Thanks Rich
The area consists of meadows, woodlands, wetlands and steep ridges all traversed by great trails of varying difficulty. The ride down to the pond is an easy and fast downhill but as you go north into Pine Mountain or further west into Hemlock Hills, the terrain can be challenging.
Trails feature twisty tight single track along rock-strewn ridges; there's even a massive slick rock section. With some hike a bike in the northern reaches—Bennetts is still a diamond in the rough but an awesome park to explore.
Fore more information go to the Fairfield Couty NEMBA website.
Update 9/20/20
NW CT NEMBA completed our final major trail project in Hemlock Hills in Ridgefield CT. Hemlock Hills/Pine Mtn/Bennett’s Pond is among the largest contiguous open spaces in Fairfield County and has become very popular. FCNEMBA has been working for many years with the Ridgefield Conservation Commission (RCC) on various trail projects, and this summer we legitimized the last of the old “social” trails. We built several reroutes to reduce erosion, and closed some “pop-up” trails to reduce proliferation and help the RCC achieve the natural aesthetic that is a foundation of their policy.
Our maps guru, Rich Coffey, has been focused on getting our trail systems updated on Trailforks. Most of our open spaces have cell-service and having updated GPS maps has been very helpful for our new members. Thanks Rich
Primary Trail Type: Cross-Country
eBikes Allowed:
No
Land Status: Conservation Reserve

Links
Activities Click to view
- Mountain Bike
63 trails
- Hike
62 trails
- Trail Running
62 trails
Region Details
- 2
- 14
- 36
- 11
Region Status
Open as of May 16, 2021Stats
- Avg Trail Rating
- Trails (view details)
- 63
- Trails Mountain Bike
- 63
- Trails Hike
- 62
- Trails Trail Running
- 62
- Total Distance
- 24 miles
- Total Descent
- 3,318 ft
- Total Vertical
- 466 ft
- Highest Trailhead
- 997 ft
- Reports
- 160
- Photos
- 26
- Ridden Counter
- 5,087
Popular Bennetts Pond / Hemlock Hills Trails
Mountain Bike Routes
title | rating | distance |
---|---|---|
Intro To Pine Mt | 3 miles | |
Nowhere Chuck Bomb | 6 miles | |
The workout | 4 miles | |
5 mile Bennetts Pond / Hemlock Hills Ride | popular ridelog | 5 miles |
5 mile Bennetts Pond / Hemlock Hills Trials Ride | popular ridelog | 5 miles |
9 mile Bennetts Pond / Hemlock Hills Ride | popular ridelog | 9 miles |
9 mile Bennetts Pond / Hemlock Hills Ride | popular ridelog | 9 miles |
6 mile Bennetts Pond / Hemlock Hills All-Mountain Ride | popular ridelog | 6 miles |
7 mile Bennetts Pond / Hemlock Hills All-Mountain Ride | popular ridelog | 7 miles |
6 mile Bennetts Pond / Hemlock Hills Ride | popular ridelog | 6 miles |
Photos of Bennetts Pond / Hemlock Hills Mountain Bike
trail: Bennett's Pond Spur - North
99 |
Aug 29, 2021 @ 11:41am
Aug 29, 2021
trail: Red Connector
135 |
Jun 14, 2021 @ 2:08pm
Jun 14, 2021
trail: Red Connector
106 |
Jun 14, 2021 @ 2:08pm
Jun 14, 2021
trail: Ives Trail - Orange Blaze
75 |
Jun 11, 2021 @ 1:08pm
Jun 11, 2021
trail: Ives Trail - Orange Blaze
81 |
Jun 11, 2021 @ 1:08pm
Jun 11, 2021Videos of Bennetts Pond / Hemlock Hills Mountain Bike

trail: Orange Access Trail - West
0:32 |
288 |
Jul 20, 2016

trail: Connector
1:36 |
865 |
Dec 31, 2013

trail: Connector
1:19 |
719 |
Nov 24, 2013

trail: Connector
2:42 |
1072 |
Nov 10, 2013

trail: Connector
0:17 |
759 |
Oct 13, 2013

trail: Connector
0:13 |
282 |
Dec 3, 2012

trail: Connector
0:13 |
440 |
Oct 25, 2012
Recent Trail Reports
status | trail | date | condition | info | user |
---|---|---|---|---|---|
Bennetts Pond North ("Pebble Beach") | Jul 25, 2023 @ 2:36am Jul 25, 2023 | Dry | chrismtbridge | ||
Up Chuck - Pine Mountain (Orange) | Apr 17, 2023 @ 12:56pm Apr 17, 2023 | Ideal | hensflo | ||
White/Orange | Apr 11, 2023 @ 8:01am Apr 11, 2023 | Ideal | hensflo | ||
Out of Nowhere | Apr 5, 2023 @ 6:26am Apr 5, 2023 | Ideal | hensflo | ||
Red Connector | Oct 2, 2022 @ 7:15am Oct 2, 2022 | Ideal | Staktup WMBA | ||
Blue Trail - Bennett's Pond | Oct 2, 2022 @ 7:15am Oct 2, 2022 | Ideal | Staktup WMBA | ||
Nice Ascent from Parking Lot | Oct 2, 2022 @ 7:15am Oct 2, 2022 | Ideal | Staktup WMBA | ||
Up and Over | Oct 2, 2022 @ 7:15am Oct 2, 2022 | Ideal | Staktup WMBA | ||
Gorge Trail | Oct 2, 2022 @ 7:15am Oct 2, 2022 | Ideal | Staktup WMBA | ||
Green Trail (West) - Bennett's Pond | Aug 27, 2022 @ 8:04am Aug 27, 2022 | Very Dry | beckley1981 |
Activity Feed
username | action | type | title | date |
---|---|---|---|---|
richjh213 | update | trail | Handcuffs Loop - Pine Mountain (Yellow) and 1 more | Sep 5, 2023 @ 9:06am Sep 5, 2023 |
richjh213 | update | trail | Up Chuck - Pine Mountain (Orange) and 1 more | Sep 4, 2023 @ 6:24pm Sep 4, 2023 |
richjh213 | update | trail | Blue Trail - Bennett's Pond and 1 more | Sep 4, 2023 @ 12:44pm Sep 4, 2023 |
richjh213 | add | trail | Yellow Trail - Pine Mountain 2 and 1 more | Sep 4, 2023 @ 11:43am Sep 4, 2023 |
richjh213 | comment | trail | Red Connector and 1 more | Aug 23, 2023 @ 8:51am Aug 23, 2023 |
Recent Comments
username | type | title | comment | date |
---|---|---|---|---|
trail | Has some very steep sections. | Aug 23, 2023 @ 8:53am Aug 23, 2023 | ||
trail | Very steep | Aug 23, 2023 @ 8:51am Aug 23, 2023 | ||
trail | Overgrown. | Jul 25, 2023 @ 2:37am Jul 25, 2023 | ||
trail | Really long climbing trail. Well designed... | Apr 10, 2023 @ 8:25am Apr 10, 2023 | ||
report | Great condition! | Apr 5, 2023 @ 6:27am Apr 5, 2023 |
Nearby Areas
name | distance | ||||
---|---|---|---|---|---|
Seth Low Pierrepont State Park and Lebowitz-Knapp Open Space | 2 | 11 | 3 | 3 | 1.3 km |
Tarrywile Park | 7 | 13 | 8 | 1 | 2.9 km |
Farrington Woods | 8 | 7 | 1 | 4.4 km | |
Bear Mountain Reservation | 3 | 7 | 1 | 7.3 km | |
Collis P Huntington State Park | 7 | 14 | 4 | 7.4 km |
Local Badges
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Completionist0 awarded
Activity Type Stats
activitytype | trails | distance | descent | descent distance | total vertical | rating | global rank | state rank | photos | reports | routes | ridelogs |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Mountain Bike | 63 | 24 miles | 3,317 ft | 10 miles | 466 ft | #1,671 | #905 | 28 | 160 | 3 | 2,290 | |
Hike | 62 | 23 miles | 3,301 ft | 10 miles | 466 ft | #1,285 | #806 | 160 | 129 | |||
Trail Running | 62 | 23 miles | 3,301 ft | 10 miles | 466 ft | #1,289 | #802 | 160 | 120 |
- By StephaneMarceau
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- bennetts pond / hemlock hills activity log | embed map of Bennetts Pond / Hemlock Hills mountain bike trails | bennetts pond / hemlock hills mountain biking points of interest
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