Where We Went: Tory Cave Falls – October Mountain State Forest, Lenoxdale, MA

When We Went: Mid-June 2020

Difficulty (Boots 1 – 10): 2 Boots, (3 Boots to get to the cave)

Trail Length: Just over 0.5 miles roundtrip

How Long it Took Us: 1.5 hours

Overview: According to writer and connoisseur of the Berkshire unusual, Joe Durwin, the use of caves as refuge was in fact, not unusual. “Caves were the original literal criminal underworld. Berkshire County has more active or “live” caves than any area in the Northeast. Tories, counterfeiters, bootleggers, “wild men” and others have all recycled them for their needs.”

And in 1776, no one needed a rocky refuge more than Stockbridge resident, and local tavern owner Gideon Smith. Smith was a Tory, a loyalist to the British crown, and his tavern (located where Wheatleigh stands today), was a popular rendezvous spot for Tory messengers passing through from Albany to Springfield in the 18th century. Then in May of 1776, Smith harbored a British POW, Captain McKay, in his home and the neighboring rebels were out for blood.

So what’s a British loyalist to do? Break for the hills and hunker down in a cave until you’re in the clear. Rumor has it that the Mohican’s brought him food and that his wife would travel nightly four miles by arduous route to parade the children by the cave on a daily basis, just to show him they were well and safe. But clear never comes for Gideon. Foolishly sticking his head out of the cave one day, he was discovered! Caught and captured, he was put to the noose three times. According to “A History of Berkshire County,” “Having fastened a halter around his neck, he was attended with due solemnity to a signpost, pulled up and suffered to remain until nearly defunct.” Told he must renounce his Tory ways, Gideon held on until the third time, saying he would “swing his hat in favor of the Colonial cause.”

The deHeredia’s, former owners of Gilded era mansion Wheatleigh, found the original Smith tavern sign on the property and gifted it to the Stockbridge Historical Library in 1902. In 1782, Gideon left another mark, purchasing a grassy knoll on Mahkeenac Road for the use as a family burial ground. Quietly overlooking the Stockbridge Bowl, it’s curious that he is not among the 22 burials and his final resting place is unknown. Gideon was 98 when he died in 1838.

Another tale, more interesting to me than Gideon’s, is about the Caveman & his sweetheart. In 1932, the cave was used as a trysting spot for two star-crossed lovers, Lenoxdale’s own Bonnie & Clyde. Sixteen-year-old Myra Holmes and eighteen-year-old Albert Felix ran away from their homes one a Friday evening in May and were missing for a week. Extensive searches were held but only glimpses of the fugitives were to be had. One Eagle headline read, “Youthful Caveman Raids Iceboxes to Bring Back Food For Young Sweetheart.” A diary was found inside Tory cave detailing the story of the couple’s escapades, including Felix’s clandestine trips to “Shacktown to get some bread, coffee, sugar, and milk.”

They were eventually found in Albany on June 3rd and returned home to their parents.

But young hearts can’t be broken. And on July 2nd, 1932, the pair ran away again!

This time they took refuge in the partially finished James Brattle Burbank house on Williams Street in Pittsfield. As icebox items started to go missing in the neighborhood, the jig was up. On July 5th, police officers raided the residence where they found Myra and Albert armed with both rifle and revolver. After a short stand-off, both were arrested and charged with various crimes, including Myra’s additional charge of “being an exceptionally stubborn child.”

For another caving adventure, check out “Gold-Diggers & Cave Crawlers

What We Dug: If there are hiking and history involved, you know I’m thrilled. Tory Cave did not disappoint. The trail to the waterfall and cave was mild and mostly easy walking. Some portions of the trail were washed out from recent rains and there were a few fallen branches to navigate around. As the path starts to go uphill, you will pass a trail for Dewy Hill on your left-hand side. Just after this path on your right, is a footpath that goes down to the stream. Be cautious! Although short, the path down can be fairly steep and unreliable for sure-footing. The cave is not visible from the trail and we found we had passed right by it. Farther up the stream were easier access points where the kids enjoyed wading and rock climbing before we turned around and hit the cave.

Calling it a cave nowadays seems overly generous. In 2013, the rain from Hurricane Irene flooded Roaring Brook and eroded any remaining cave that was left after the landslide. The area is a little tricky to get to but the beauty makes it worth the fumbling footwork. I can almost see Myra and Albert splashing each other at the edge of the pool, wary of snapping twigs coming to interrupt their idyllic getaway. I wonder what happened to those two…if they ever ended up together or were doomed from the start.

What We Could Do Without: It was hot and humid. Add water to the mix and you’ve got mosquitoes. Buzzing, bloodthirsty blaggards, impervious to the densest plumes of repellent. I actually think some of them like it. Skeeters put a damper on shit for sure but we just keep marinating in citronella and hoping for the best.

Keep Your Eyes Peeled For: Walking ferns, hemlock, pine, red efts, wood frogs, mountain wood-sorel, water striders, rainbow and brook trout

Must Know Before You Go’s: Parking and trailhead are just before a small bridge. There is no parking area so use caution when parking on the shoulder. Trailhead heads east upstream along Roaring Brook. No facilities. Leashed dogs okay.

Directions: From Route-7 in Lenox, turn onto, heading east on New Lenox Road for 1.8 miles. At the intersection of East New Lenox Road and New Lenox Road, turn right onto Roaring Brook Road. Head south for 0.4 miles, just before a small bridge. Trailhead is to your left. GPS: N422316.08 -W731416.17

Website: October Mountain State Forest

Resources: lenoxhistory.org, “History of Berkshire County” by Godfrey Greylock, Berkshire Eagle Oct. 31, 1976, Berkshire Eagle May-July, 1932, These Mysterious Hills – Joe Durwin