Exploring Sharon Connecticut’s Epic Land Trust Trails

For those who have been fortunate enough to wander in the hills of northern England, you’ll quickly recognize the visual parallels between that magical region to the rolling and open landscapes of Sharon, Connecticut.

In this post, you’ll find 11 different land trusts worth exploring in Sharon, Connecticut, a beautiful corner of northwest CT. I’ve been to several land trust trails in Connecticut but these in Sharon are the prettiest I’ve seen so far!

In downtown Sharon, a grey stone library offers its free literary wares, a perfect little cafe serves up caffeine and pastries, an elegant market provides all essentials, and an amazing BBQ spot makes you question whether you’re actually above the Mason-Dixon line.

It’s all enough to allow a whole day to slip away walking up and down the town green, encircled by perfectly cracked sidewalks. But it’s beyond Main Street where we’ll explore below.

(To help plan your visit, check out my post all about a day trip to Sharon, Connecticut!) 🥐🥾

Tight winding roads coil and heave between open farm fields and whimsical 18th and 19th-century mansions. Rock walls, some crumbling, assembled centuries ago from stones hewn from farm fields, guide us into rural Sharon and to the 11 distinct preserves that comprise the Sharon Land Trust.

Not only do these beautiful preserved properties offer up vista views as glorious as nature creates, but some of these trails are legitimate hikes with extended mileage and elevation gains!

Bring the kids, bring the grandparents, bring the dogs.

Let’s explore!

11 Land Trusts in Sharon Connecticut

1. Garrett Goodbody

Parking for Garrett Goodbody Preserve can be found off of Millerton Road just outside of downtown Sharon. Here you’ll ready yourself for a blissful 2 mile stroll in and amongst 107 peaceful acres, all while gaining about 515 feet in elevation. 

After a brief .2 mile walk up the gentle slope of a wide open field, expansive vistas of cleared farmland sprawling in all directions, you’ll come to a juncture. The direction of choice is entirely up to the visitor, with each providing incredible views, but I would set off on a counter-clockwise orientation. 

2 incredible highlights await within this forest. The first is reached in about 1 mile and provides dramatic easterly views of the Sharon Valley and Mudge Pond. 

The second overlook is reached in another .5 miles and boasts westerly views of the Hudson River Valley as it lies gracefully in Millerton, New York.

Emerge from the woods to gorgeous southerly views of the surrounding landscape and head on back down the trail to the parking area. 

2. Benton Hill

To reach Benton Hill Preserve, one travels a road that carves its way between competing awe inspiring mansions and incredibly manicured landscapes. This area, including the captivating 9 hole Sharon Country Club, vibes rural opulence in a way few other places in Connecticut do. 

Off of Benton Hill Road sits the parking spot for this little 2 mile hike. A beautiful northerly view is there to greet visitors from the get-go. Breathe easy amongst these 72 acres.

This trail dips and dives through mystical tunnels of tightly walled foliage. These dark and wild tunnels begin and end abruptly, either welcoming you in from a bright wide open field or spitting you out into one. The effect is like coming up from below decks on a ship, darkness into light. 

You’ll pass through several beautiful fields, giant trees marking their boundaries in the distance. As well as a few shaded, tunneled hallows. 

At about the .75 mile mark you’ll reach a trail juncture. As always, your call as to which way you’d like to go with nothing being lost to one decision or the other. 

Circle around through a lush diverse forest, reaching the main trail again in about half a mile. Hike back out the same way you entered, enjoying all the views in reverse.

3. Mary Moore

Singular places where you can enjoy amazing vista views of 3 different states at once are few and far between in the state of Connecticut. Not to disparage the generally low lying Constitution state, but to glorify the Mary Moore Preserve as one of the more special properties curated by Sharon Land Trust.

While enjoying the sights of the Catskills to the west, Connecticut’s Riga Plateau and highest points to the north and west, and the shrouded Berkshire Mountain’s of Massachusetts receding into the north you’ll gain about 530 feet in elevation while traversing over 3 miles of trails nestled within 181 acres. 

Immediately upon setting out on the trail from parking along Williams Road you’ll know you’re somewhere special, surrounded by peaceful pristine farmland and gentle doe-eyed livestock. 

At about .7 miles you’ll reach the pinnacle with the above multidirectional display of natural beauty in full effect. A fantastic place to enjoy a morning coffee or a picnic, the viewing area wide open, even offering a much earned sit on a beautifully constructed and graciously donated wooden bench. Enjoy this stretch until again entering the forest and looping around counterclockwise ultimately reaching the parking area.

All of these preserves offer windows into New England’s past and it’s easy to feel you’re walking through centuries old landscapes, with little to nothing to break the welcome illusion. 

4. Twin Oaks

Off of Mudgetown Road sits the parking area for Twin Oaks Preserve. A pristine New England farm field that hosts two natural sentries in the Twin Oak trees that stand tall in the field’s middle ground. 

The white oaks that grow on the property today are replacements of 2 oaks that had graced the rolling landscape since before the American Revolution. The original oaks both met a natural end in 2013 and were replaced by the ones that are seen there today. 

Today there are generously donated benches along the trail, placed at prime vista viewing locations, allowing for an exceptionally relaxing and reflective little hike in the hills. 

There are several routes and trails that follow the circumference of the field but also bisect it in areas. The circumference loop is an easy and amazingly well worth it 1 mile, gaining about 180 feet in elevation while traversing. 

5. Von Ahn

Just prior to entering Millerton, New York driving north on Millerton Road awaits the parking area for Von Ahn Preserve. Park, get your boots tied tight and ready yourself for a deceptively arduous little climb in these lush hills. 

Amongst the 170 acres of this preserve is a 2.5 loop trail that will lead you up about 616 feet into the woodlands, over cleared fields, and past several viewing areas of the surrounding landscapes. There is a network of trails on this property, leaving it up to the visitor to choose which route they’ll take over and through these hills.

The views are primarily western facing and offer fantastic windows of the surrounding farmland and glimmering Indian Lake. 

Again, donated benches mark the vista viewing areas and are a welcome sight for those looking to take a well deserved load off.

6. D’Alton 

101 West Woods Road #1

70 acres, 3 miles of trails (open to both equestrian and pedestrian use)

Difficulty level: Moderate

Elevation gain: 203 feet

7. Skiff Mountain North

583 Skiff Mountain Road

197 acres; 1.2 miles of trails (open to both equestrian and pedestrian use)

Difficulty level: Easy

Elevation gain: 75 feet

8. Bucksbaum 

Lambert Road (1/4 east of the intersection with Amenia Union Road)

45 acres; 1.2 miles of trails

Difficulty level: Easy

Elevation gain: 300 feet

9. Sharon Mountain

189 East Street 2 additional small parking areas are located at 201 Bowne Road and 100 feet west of the East Street intersection on Tichnor Road.

140 acres; 2.5 miles of trails (open to both equestrian and pedestrian use)

Difficulty level: Easy

Elevation gain: 278 feet

10. Hamlin

19 Stone House Road

278 acres; 2.5 miles of trails

Difficulty level: Moderate

Elevation gain: 386 feet

11. Wike Brothers

Parking area across from 38 White Hollow Road

268 acres; 0.5 mile of trails

Difficulty level: Easy

Elevation gain: 389 feet

I hope you enjoyed this list of land trusts in Sharon, Connecticut!

And I’m sure you now have at least a few you want to visit.

I’ve found that the itinerary for the perfect day outdoors consists of pairing several of these magical preserves together, driving on Sharon’s perfectly scenic country roads from one to the next. You’ll be surprised at how quickly the miles and memories begin to add up! 

Happy exploring!