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 33rd annual XIH took place on June 7, 2025 and ranged 18.2 miles from Chilmark Pond Preserve to Eastville Point Beach. Approximately 135 people participated in the cross-island trek. Some 99 started; 35 completed the entire hike. The route passed along 23 conservation properties and 5 named ancient ways. 

The next XIH will take place on Saturday, June 6, 2026

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:

2026 Cross-Island Hike

This year’s hike begins at Eastville Point Beach and concludes 20.9 miles to the southeast point of Chappaquiddick at Wasque Reservation. The hike starts at 8:15 AM and finishes at 4:20 PM. Participants should use the checkpoints on the 2026 XIH map to determine which part(s) of this year’s hike best suits their schedules, interests, and physical capabilities. 

2026 XIH Map

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

Eastville Point Beach (Town of Oak Bluffs)                                                                    Caroline Tuttle Preserve (SMF) 
Ramble Trail Preserve (Town of Tisbury)                                                                        Slater Preserve (SMF)
Bare Hill Preserve                                                                                                              Ames Preserve (SMF)
Sailors Burying Ground Road (AW)                                                                                 Three Ponds Reservation 
Road to Wapatequa (AW)                                                                                                 Cove Meadow Preserve
Great Rock Road (AW)                                                                                                       Toms Neck Preserve
Wapatequa Woods Reservation                                                                                       Mumcheag Creek Preserve (SMF)
Beech Tree Preserve                                                                                                           Poucha Pond Reservation
Southern Woodlands Reservation (OB)                                                                           Wasque Reservation (TTOR)    
Old Holmes Hole Road (OB)                                                                         
Felix Neck Wildlife Sanctuary (Mass Audubon)                                                                          
Felix Neck Preserve                                                   
                                                                          
                                                                           

This map shows​​​​​​​ ​​​​​​​t​​​​​​​h​​​​​​​e​​​​​​​ ​​​​​​​r​​​​​​​o​​​​​​​u​​​​​​​t​​​​​​​e​​​​​​​ ​​​​​​​o​​​​​​​f​​​​​​​ ​​​​​​​t​​​​​​​h​​​​​​​e​​​​​​​ ​​​​​​​h​​​​​​​i​​​​​​​k​​​​​​​e​​​​​​​.​​​​​​​ ​​​​​​​​​​​​​​

The early portions of the hike (segments A-B and B-C) meander through flat terrain surrounding Lagoon Pond.  The shoreline of Lagoon Pond will be traversed.  The width and depth of the crossing varied with shoaling.  The tide will be low at the time of the hike but participants in this segment should plan on at least 4-to-6 inch deep water for several places.  Unless you have your Wellies, plan on your feet getting wet, whether covered or exposed.  Section D-F is a long jaunt from Lagoon Pond to Church Street in downtown Edgartown.  G-H is the last leg of the hike and encompasses much of the conservation land that makes up the smaller island of Chappaquiddick.  But be advised, once on Chappaquiddick, the walk is still 8.5 miles. 

The morning break will be at the Southern Woodlands Reservation.  The lunch break at the Church Street VTA is a little over half-way through the hike and the afternoon break at the Chappaquiddick Community Center at nearly two-thirds.  Bathroom facilities will be at all three locations. 

Parking and frequent bus service is available for arriving at Eastville Point Beach. 

Well-mannered, leashed dogs are welcome to accompany their owners from segments A-D and then again from F-H.  

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 bveno@ marthasvineyardlandbank.com 

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!