Annual Cross-Island Hike

The Land Bank Celebrates National Trails Day — the First Saturday of June

What is the XIH?

Each year since 1993, the land bank has observed National Trails Day — the first Saturday of June — by conducting a day-long hike across the island to expose people to the network of trails that connect the island’s many conservation lands and public properties. Usually the hike will include sections along dirt or paved roads, but sometimes may include shorelines, steep grades and sections of overgrown vegetation (possibly including poison ivy). Hikes sometimes include stretches across private properties with the generous permission of the owners for the day of the hike only. This is a day-long, guided hike that differs each year and is ordinarily less than 20 miles in length and most participants elect to walk only a portion of the hike’s route, using the itinerary times and information provided on this website to plan their personal starting and ending points.

The next XIH will take place on Saturday, June 1, 2024 

What to Expect

This is not a guided nature walk. Due to the length of the hike, the pace is briskly led. The hike leader marks turnoffs and intersections with colored tape for hikers to follow. About every hour, the hike's leader will pause a few minutes to provide opportunities for slower hikers to catch up. Hikers are encouraged to walk at their individual comfort levels. Most participants opt to walk only a portion of the ROUTE. Approximated times and distances for segments of the hike are provided with the map of the route to help people plan how they wish to be part of the hike. 

Sturdy shoes, water bottles, insect repellent and sunscreen (or rain gear) are recommended. Well behaved, leashed dogs are welcome, unless otherwise noted.  

There is a 30-minute lunch break and 15-minute breaks mid-morning and in the afternoon. Hikers are responsible for their own food and water. To augment hiker’s provisions, the land bank normally has some fruit and water at the morning and afternoon breaks. Efforts are made to have restrooms available at the breaks, but this is not always possible. Restroom availabilty will be identified in the hike’s details. 

Long hikes always have to cross roadways and frequently require walking alongside some roads for extended stretches. Hikers need to remain alert.

Transportation to and from the hike is the responsibility of the participants. Parking is often very limited at starting and ending points. Please check the VTA bus schedules. 

​​​​​​​Details as to the most recent XIH follow:​​​​​​​

2023 Cross-Island Hike

This year’s hike begins at the Long Point Wildlife Refuge beach and concludes 17.3 miles later at Tashmoo Beach. The hike starts at 8:15 am and finishes at 3:00 pm. The morning break is at the Old County Arboretum across from the West Tisbury School (checkpoint C). The lunch break (checkpoint E) is at Holmes Hole Road near the Tisbury Dog Park. The afternoon break is at Veteran’s Park next to the Post Office (checkpoint F). 

Restrooms are available at the Long Point Wildlife Refuge visitor center and should be used prior to the start. The hike will not pause as it passes near the visitor center entering the woodlands. Port-a-potties may be available at the West Tisbury school grounds (checkpoint C) and will be available at the noon break (checkpoint E). A few restroom locations are near Veteran’s Park (checkpoint F). 

No dogs are allowed at the beginning of the hike in Long Point Wildlife Refuge.  

Questions about the Cross-Island Hike can be sent to Bill Veno:  veno@ mvcommission.org 

2023 itinerary:

use the following information to plan which portions of the hike to participate in and to make transportation arrangements. 

8:15 am ​​​​​​​​​​​​​​- Segment A (3.6 miles) Long Point Wildlife Refuge to Edgartown-WT Road​​​​​​​​​​​​​​
​​​​​​​This segment traverses the Trustees of Reservations (TTOR) expansive oceanfront refuge (NO DOGS ALLOWED) using an old access road normally not accessible for the public to walk on (permission to use only for this day’s hike). The route follows the Watcha Path/Scrubby Neck Path ancient way, portions of which are traveled by vehicles. The terrain is mostly level with a few rolling hills.
​​​​​​​Directions: ​​​​​​​​​​​​​​Allow sufficient time to reach the starting point. Off-season vehicle access from Edgartown-West Tisbury Road is from Deep Bottom Road, then left on Watcha Path and right on Thumb Point Road, then follow signs and stay left to Trustees’ parking lot before the visitor center. This is 2.5 miles of narrow, often single lane, dirt roads. Note that the hike’s start on the coast is another half-mile beyond the visitor center. ​​​​​​​

9:30 am - Segment B (2.4 miles) Edgartown-WT Road to Old County Arboretum​​​​​​​​​​​​​​​​​​​​​
​​​​​​​This segment passes through the Manuel F. Correllus State Forest, mostly along an old cart path, and concludes at the Land Bank’s Old County Arboretum, across from the West Tisbury Elementary School. There is a short, steep downgrade a few minutes into this segment that can be bypassed by using the parallel paved shared use path.
Directions:  This departure checkpoint does not have any parking nearby, nor is the location suitable to pull off the road for pick up or drop off. Within 100 feet of the hike’s route along the north side of the Edgartown-West Tisbury Road, an asphalt walkway extends west to the Youth Hostel, the ball field at the West Tisbury fire station, and continues farther west. The VTA #6 bus passes by hourly in both directions.

​​​​​​​​​​​​​​10:30 am - Segment C (2.0 miles) Old County Arboretum to Old County Road and Great Plains Road​​​​​​​​​​​​​​​​​​​​​
This segment begins along the paved shared use path before crossing alongside Whippoorwill Farm to the Old Holmes Hole Road ancient way passing along the John Presbury Norton Farm and intersecting the Stoney Hill Path. The route is flat and treelined.
Directions:  There is limited parking at State Forest’s Gates 21 and 22. The West Tisbury School parking lots are across Old County Road but may have limited space due to youth soccer. VTA #2 passes here northbound and VTA #3 passes southbound.  

​​​​​​​​​​​​​​11:05 am - Segment D (2.1 miles) Old County Road to Holmes Hole Road​​​​​​​​​​​​​​
This segment follows two ancient ways – Stoney Hill Path and Old Back Road, a.k.a. Old Holmes Hole Road – through the land bank’s Tisbury Meadow Reservation and concludes at the section of Holmes Hole Road that is now a typical dirt roadway. There is one steep decline of just a couple steps that require caution and possibly a steadying hand from a fellow hiker.
Directions:  The hike is along Stoney Hill Path that crosses Old County Road between the road’s intersections with Great Plains Road to the east and James Way to the west. There is no parking at or along Old County Road. VTA #2 passes here northbound and #3 passes southbound.  

​​​​​​​​​​​​​​12:10 pm - Segment E (3.2 miles) Holmes Hole Road to Veterans Park​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​​
This segment courses through the land bank’s Wapatequa Woods Reservation to an ancient way connecting its namesake, Old Sailors Burying Ground, to Bare Hill Preserve, then crosses Edgartown-Vineyard Haven Road to Ramble Trail Preserve and Sheriff’s Meadow’s Brightwood Park, then alongside a dirt road and a paved road along the edge of the West Arm of Lagoon Pond to Tisbury’s Veterans Park. There are two steep ascents before reaching Edgartown-Vineyard Haven Road.
​​​​​​​Directions:  From State Road take Holmes Hole Road .4 mile to where a paved drive intersects on the right. Park alongside the dirt Holmes Hole Road as space permits. Holmes Hole Road dead ends a few hundred feet beyond the paved drive, at the John G. Rogers Memorial Dog Park. Please DO NOT PARK in the parking lot at the dog park.

​​​​​​​​​​​​​​1:30 pm - Segment F (1.6 miles) Veterans Park to West Chop Woods​​​​​​​​​​​​​​​​​​​​​
This segment traverses downtown Vineyard Haven via an alleyway, proceeding .6 mile along the harbor’s edge and then courses along a short stretch of paved roads and the dirt, Old Lighthouse Road to West Chop Woods.
Directions:  We exit from the northeast corner of Veterans near the post office and Cumberland Farms. Rather than tie up spaces provided for park users, consider the VTA bus. Its main transfer hub from all points is at the end of Water Street is .25 mile away, and this segment of the hike proceeds directly to that area before continuing along the harbor.

​​​​​​​​​​​​​​2:05 pm - Segment G (2.4 miles) West Chop Woods to Tashmoo Beach​​​​​​​​​​​​​​​​​​​​​
This segment follows the powerlines for nearly one mile. The surface has areas of loose sand. There are a dozen gates at street crossings with clearances generally 4 to 5 feet from the ground, so hikers need to duck in order to pass—there is not usually sufficient room to squeeze by at gate ends. The hike continues along the Herring Creek Road, mostly along a pathway separated from the motor traffic, passing by Wilfrid’s Pond Preserve and Tashmoo Preserve before concluding at Tashmoo Beach.
Directions:  We exit the southwest corner of West Chop Woods along Franklin Avenue, near the property’s trailhead where there is limited parking. The VTA #10A passes southbound. Vehicle access to Tashmoo Beach is via Daggett Avenue west to Herring Creek Road. Parking at the beach can be limited.

​​​​​​​​​​​​​​3:00 pm - Finish at Tashmoo Beach​​​​​​​

​​​​​​​​​​​​​​​​​​​​​Previous Hikes:

Below is a list of the XIHs since they started in 1993 and links to maps from several of those hikes. For some years, only the morning or afternoon segment is provided. Only hikes and segments not involving any special permissions from landowners have been selected. We hope these will provide ideas for people to explore or redo portions of previous hikes, or to string together their own customized hike of whatever distance. Mapping has changed over the years. The early maps were just notes for land bank staff conducting the hikes. It was not until 2008 that maps were made for participants. People are cautioned to check the current land bank map or the TrailsMV trail app to verify the trail routes as they exist today. Enjoy the outdoors!