On My Way: Biking Pennywise Path

There’s nothing like the feel of a trail under your tires.


I had wanted to be back in the saddle for some time. It had been a few months. Usually, a few times over the winter on a Sunday afternoon, I bundle up and set out. Not so much this year.

I was looking forward to the trail under the tires, the wooded turns and hills. I was looking forward to the escape and workout of a good bike ride. 

My mind was set upon the Pennywise Path Land Bank property. I had stumbled on Pennywise in the early fall on another ride. I wanted to return and explore.

I called my brother and asked if he would like to join me. My brother and sister five years ago or so gave me a Trek mountain bike for Christmas. What a gift! I have logged a lot of miles since then. Mountain biking trails are all over the Island. All one has to do is look. A new world opened.

I met my brother Douglas on the Edgartown–Vineyard Haven Road near the Bare Hill Land Bank property. The early spring day a few weeks ago was partly sunny with a chill in the air. I wore bike shorts.

We took the bike path in the direction of Edgartown, and soon turned onto a residential street. A paved road with speed bumps took us through a quiet year-round neighborhood. We chatted.

At the end of the street, we found a trail into the woods. A steep, short hill required dropping into a low gear and standing up on the pedals. After the short ascent, the trail was narrow and fast.

We turned off onto a branch trail. I am always glad to have a good bike on this rocky, steep downhill. The bike is put to the test.

A shot of adrenaline coursed through me, and I picked up momentum. The bike shook and bounced over the rocks. I held a solid grip on the handles. I let the bike go right to the edge of my comfort level — my hand ready on the rear brakes.

I emptied onto another trail. A few seconds later, I tore off on a trail to the right. The trail ascended some and flattened. Soon I was working the pedals.

We passed along the fenced side of a pasture, which we affectionately refer to as the field of goats. The goats were out this day.

The trail took us into the Wapatequa Woods Reservation, where short uphills and downhills and tight turns made for good riding. I was glad to be on my bike in the woods.

After a few miles, we came unceremoniously onto Stoney Hill Road.

We biked up Stoney Hill, and after less than a mile, we turned back into the woods. The rock-covered, uphill trail is difficult terrain. I lowered my gears and went to work. I felt the burn in my thighs.

This trail brought us into the Margaret K. Littlefield Greenlands.

The Greenlands is a sanctuary of oak forest. A network of trails makes for fun bike riding. One can move along here without too much effort. 

Douglas, a faster biker, was waiting for me at the State Forest bike path, where the Greenland trail spilled out.

We went a short distance on the paved bike path and turned onto a fire lane. We biked past the Frisbee golf course to the bike path along Barnes Road, and crossed Barnes at the State Forest headquarters entrance. 

We found the trail system called Twisty.

Twisty is a terrific web of trails. I had not biked Twisty in a long time. I was looking forward to the continually turning trails, and I also wanted to see how Twisty survived the Department of Conservation and Recreation’s spate of trail closures.

All last summer and into the fall, every time I went out I was disappointed to find another beloved trail closed. The names of the shuttered trails are endless — Explorer, Barn Owl, Aviator … According to DCR, the trails were not permitted properly.

Twisty remained somewhat intact. 

Felled trees and DCR signposts did shut down many of the trails, but still one could enjoy a good ride. We biked Twisty for 20 to 30 minutes. We went through a charred section of forest that had every indication of a controlled burn. Douglas waited at the junctions.

Gradually Twisty took us toward the E-VH Road. We turned south on a fire lane.

Fire lanes can be difficult riding. Patches of loose sand can bring one to an abrupt halt that can threaten to topple you. The only recourse is to drop into a low gear, stand up, and struggle through. Or go off to the side, if possible.

Not too far ahead, we found Dr. Fisher. Dr. Fisher brought us to one of the many Island developments situated between the E-VH roads and the Edgartown–West Tisbury Road. We crossed a paved drive, and arrived at the Vineyard Golf Club.

We had been here many times, but we never had known of the nearby Pennywise. I was determined. I looked at TrailsMV, and the site showed a clear trail to the left.

The reward was greater than expected. We came out of the woods onto a glorious open expanse of field carved out of the forest with a few trees. We both took a moment to catch our breath. We were in awe.

We biked a trail through the center. The wind blew across the open field. We took our time. Pennywise was not a big property, and it did not take long to go from one side to the other. We looped back around on a side trail. We rode slowly. The hidden property had a mesmerizing bent, and I was filled with a sense of peace. 

Back on Dr. Fisher, we biked a straight shot to forestry headquarters. I was worn out. After two hours, my thighs were fatigued, and my strength was ebbing. I had no interest in a longer route.

We recrossed Barnes Road and returned through the Greenlands on a way that dumped us onto the perimeter of Thimble Farm. We biked Stoney Hill to Hay Path Road. 

The ascent of Hay Path was a challenge. I was exhausted.

We re-entered the woods at the top of Hay Path. The trail took us back to the field of goats and then onto a dirt road. We went past the Sailor’s Burying Grounds. A last set of trails brought us in the area behind the Vineyard Haven solar array. Mud Puddle Road brought us to the E-VH Road. 

It was a few minutes home. I unsaddled. My legs were jelly. I brought my bike around to the back of my house. I lifted it over the fence into my backyard. I was spent.

I felt the exhilaration of the ride. The varying trails were imprinted upon me. My body felt the satisfaction of the effort. We had escaped for a while on the wooded trails. We had sought out and explored Pennywise. Pennywise lived up to its name — a shiny penny looking up at you.