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 32nd annual XIH took place on June 1, 2024 and ranged 19.2 miles from Hillman’s Point Preserve to the Chilmark Pond Preserve. Approximately 135 people participated in the cross-island trek. Some 99 started; 42 completed the entire hike.  The route passed along 17 conservation properties and 5 named ancient ways. 

The next XIH will take place on Saturday, June 7, 2025.

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 hikers’ 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:

2024 Cross-Island Hike

This year’s XIH begins at Hillman’s Point Preserve on Lake Tashmoo (across the lake from where the 2023 hike finished) and concludes 19.3 miles later at the Chilmark Pond Preserve. The hike starts at 8:00 AM and finishes at 3:20 PM.

2024 XIH Map

Seventeen conservation properties (land bank properties, unless otherwise noted) and five protected ancient ways (AW) are included in this year’s hike:

Hillman’s Point Preserve (checkpoint A on map)

Phillips Preserve (SMF)

Ripley’s Field Preserve (checkpoint B)

Shubael Weeks Road (AW)

Red Coat Hill Road (AW)

Blackwater Pond Reservation

Wompesket Preserve

John Presbury Norton Farm (checkpoint C)

Manaquayak Preserve (checkpoint D)

South Indian Hill Woodlands Preserve

Rogers Path (AW)

Old Courthouse Road (AW)

Square Field

Brandy Brow (WT Conservation Commission)

Tiasquam Valley Reservation (checkpoint H)

Meeting House Road Association (before checkpoint I)

Tea Lane Farm (checkpoint I)

Holman Road (AW)

Middle Line Woods Preserve

Peaked Hill Reservation (checkpoint J)

Fulling Mill Brook Preserve

Chilmark Pond Preserve (checkpoint K)

The AM break is at the Public Safety Building in the West Tisbury business district (checkpoint E). The lunch break is at the West Tisbury Town Hall (checkpoint G). Public restrooms are available at the morning and lunch breaks. The afternoon break is at Middle Line Woods Preserve but is not a timed checkpoint. Participants are encouraged to use the checkpoints on the 2024 XIH map to tailor a shorter hike that best suits their schedules and interests. Please consider that the afternoon sections traverse some of the island’s hilliest (i.e., strenuous) terrain.

Allow sufficient time to be dropped off at Hillman’s Point. Do not plan on being able to park a vehicle there. Similarly, parking at Chilmark Pond is very limited. The most parking options are at the West Tisbury business center and town center, and the Chilmark parking lot on the Tabor House Road (next to Middle Line Woods before checkpoint J). The VTA bus schedules may help in planning pick-ups and drop-offs. The VTA #5 bus passes by Chilmark Pond at 3:25 towards West Tisbury town center. This may be an inducement for use to finish before 3:20!

Well-mannered, leashed dogs are welcome to accompany their owners.

The hike route will also be available on the TrailsMV app, so participants can monitor their progress.

Questions about the XIH can be sent to Bill Veno at veno@ mvcommission.org.​​​​​

​​​​​​​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!