On My Way: Sepiessa and Long Point

Going out on a cross-Island biking adventure.


We heard the waves crash at Sepiessa Point looking out over Tisbury Great Pond. We saw the waves crash at Long Point looking out over the Atlantic Ocean. I met my brother Douglas at our usual spot on the Edgartown–Vineyard Haven Road. We biked a ways, and then turned on one of the side streets. We biked to the end through a quiet year-round neighborhood, and accessed an unnamed trail — one not on the maps — into the woods. We went up a steep incline which took us to a fast and narrow trail with fair-size rocks that tested one’s comfort in the saddle. The section of trail was a good warm-up for what was to come.

After a half-mile or so, and after picking up Douglas’s pannier, which had fallen off his bike onto the trail, we went left. We descended a steep incline at high speed, bouncing over a thrilling, rock-strewn trail. The trail fed onto another trail. We went no more than 20 yards, and took a right upward. Soon we were biking the Land Bank’s Wapatequa Woods Reservation. There are a number of trails in Wapatequa. They tend to turn, ascend, and descend, with rocky sections making for a challenging and fun ride.

We came out onto one of the two Stoney Hill Road trailheads. We biked the easy section of dirt road to Stoney Hill Path, which one finds off to the left. Stoney Hill Path goes up steeply. I turned into lower gears and stood up on my pedals. The path is covered with patches of small to midsize rocks, making the ascent more difficult. After a near 180° turn some way up Stoney Hill Path, we were cruising a bumpy downhill trail in the Margaret K. Littlefield Greenlands. The trail carried us along for a while. Then we veered right. 

One may think of an indoor track when thinking of this next trail. The surface is level and smooth without scatterings of rocks. One flies along. Some great turns offer a bank on which to ride. The trail here always goes longer than one thinks. But soon we were out of the Greenlands and on the State Forest paved bike path. We took the path a few minutes before returning to the woods.

Our next trail was a gem of a trail. One does not expect the trail where one finds it. The trail is as peaceful as can be, and makes easy snaking turns. One is on a stroll in the woods, albeit on a bike. Unfortunately, the trail does not last long. We came out onto a fire lane. We were not exactly sure how to go, though we did know the general direction. We found our way on a number of fire lanes to the paved bike path near Old County Road. 

We continued our venture south. Elias Lane took us to Old County Road. Old County Road took us to the Edgartown–West Tisbury Road. The West Tisbury Road took us to New Lane. New Lane put us on Tiah’s Cove Road. Not more than five to 10 minutes on Tiah’s Cove Road, and we were biking down Clam Point Road to Sepiessa Point — part of the Land Bank Sepiessa Point Reservation. We left Clam Point Road onto one of the Sepiessa trails to make the final distance to Sepiessa Point. Here we stopped for a few minutes.

We were looking out over the Tisbury Great Pond. The serenity of the pond was almost tangible. The tide was high, with the water up nearly to the back of the beach. The pond surface was a mirror to the light in the sky. Only a wisp of wind was evident on the pond further out from the shore. The fall day was beautiful. There are beautiful summer days. But a beautiful fall day in my opinion is hard to rival. This was one of those days.

The cloudless sky was crisp, and a light and deep blue. The sun was radiant, and I relished the warmth, though it was not too hot by any means. A hint of chill also was in the air. We took a few minutes to enjoy the scene and to have a drink of water. “Do you hear the waves?” Douglas asked. I looked across the pond to the South Shore. “Yes, I did not notice what I was hearing, though,” I responded. I listened to the far-off quiet crash.

We took the Sepiessa trails back to their beginning. Rather than going back on Tiah’s Cove Road, we took a dirt road right in an easterly direction toward Long Point. Douglas had done the ride before, and knew the way. The dirt driveway sort of road lent no sense of its location. The road turned frequently, and the woods were up to the sides. We could have been anywhere on the Island. Thick sand was in the middle of the road, making crossing over difficult. 

We came to a wider dirt road. A friendly four-man peloton charged along in the opposite direction. We waved hello as we passed. We went by any number of driveways. At a nondescript road juncture, we turned south. Soon we came to the parking lot of Long Point. We continued on the sandy path. We left our bikes when the sand became too thick. We walked over the dune to the beach. The scene before us was gorgeous. The sunlight sparkled. The mighty ocean was a wonderful blue. Long lines of small surf crashed onto the shore. The tan beach was empty. We stood in awe.

We watched and listened to the waves. Nothing could be said. We looked out over the vast ocean and along the wide sweep of the beach. We took in the vibrant colors. I looked up to the Aquinnah Cliffs. They were farther off than I thought. I could just make out the terminus of the beach and the hazy contour of the Cliffs. A dune ran most of the length. After taking a moment to appreciate fully what was before us, we decided we should be on our way. We walked back over the dune to our bikes. We were two hours plus into our ride.

We came back out north on the dirt roads to the West Tisbury Road — near the airport, as it turned out. We took the paved bike path to Barnes Road, and then biked the Barnes Road bike path to the end of the airport fencing. We had two options. We could go to the roundabout and take the paved bike path home, or we could return on the more demanding ride on the trails through the woods. There was no question as to which route. Out of respect for the ride we had done, we had to come back on the trails. 

I was tired from the now nearly three hours. My legs were sore. My back was more sore. I decided I had some left in the tank, though. We turned at the end of the fencing. We biked the paved path back to the trailhead of the Greenlands. We went back on the same Greenlands trail. We took a connector trail from the Greenlands to Thimble Farm. We biked along the side of Thimble Farm to Hay Path road.

Hay Path and then Bridle Path roads are a grueling ascent after a long, strenuous ride. I dropped into lower gears. I wondered where the strength was going to come from. Douglas pulled ahead. I persevered to where the hill levels off some, and caught my breath. I made it back to the trailhead into the woods. Thankfully, it was now an exciting downhill for a way. 

We returned home through a portion of Wapatequa, and not long later past the Sailors Burying Grounds. A few more trails delivered us to Mud Puddle Road. We came out of Mud Puddle to the Edgartown road. We were at the end of our ride. Each of us was within a half-mile of our homes now. We felt the pleasing exhaustion of our bodies. We smiled as if in a shared secret. What an awesome ride.