Explore the Tompson Street Reservation on the North Shore

Activity Type: Hiking, Local Walks, & Trail Running | Hiking
Difficulty: 4 - Moderate
Trip Leader(s): Jonathan Unger, Marjorie O'Malley
Registration Type: Application
Please Click Here to RSVP: https://activities.outdoors.org/a5UVX0000016FDV
Register By: 5/22/2026
Audience: Everyone

Description: Join us as we explore the Tompson Street Reservation, Greenbelt's largest property at 338 acres, located in Gloucester, MA. On this hike, you will experience a rugged landscape that showcases Cape Ann’s unique geography. We will navigate our way through a mixture of historic footpaths and cart roads that wind through young hardwood forests and shrubs. Additionally, we will hike over many exposed bedrock slabs and granite ledges to scenic vistas, and through lower wetland environments featuring vernal pools and swamps.
Of particular historical significance is the Tompson Street Cart Path, which is the spine of the Reservation and dates back to the early 1700s. As we hike along this Cart Path, we will visit the site of the Second Parish Church and Meetinghouse, established in 1716, and recount the story of Reverend Samuel Tompson, a driving force behind its creation and its first leader.
The terrain on this hike is challenging. Trails are often rocky, some of which are through boulder fields, with numerous ups and downs. You should be comfortable scrambling (using both your hands and feet to climb or descend) for short lengths of the trail. Additionally, the t rail is sometimes faint and narrow, and traversing it is at times akin to bushwhacking. Rewards include views of Gloucester Harbor and Ipswich Bay from the tops of Sunset Mountain and Eagle Rock, and of the Red Maple Swamp's captivating scenery from its shores and from elevated boardwalks.
What to Expect This hike is approximately 6 miles long , with an elev ation gain of approximate ly 600 ft . Total time for the hike is expected to be approximate ly 4 - 4.5 hours , including breaks and lunch, with an average speed around 1.5 to 2.0 MPH , depending on trail conditions and the speed of the slowest hikers in the group.
What to Bring You should plan on bringing the following:
day pack/backpack (no back sacs with draw strings) at least 2 liters of water lunch and snacks rain/wind jacket and pants first aid and anti-blister supplies multiple layers of moisture wicking clothing appropriate for May weather conditions (no blue jeans or cotton) sturdy, waterproof hiking boots with good tread (no sneakers or sandals) wool socks (one pair on your feet & an extra pair in your backpack is recommended, if the first pair gets wet) hiking poles are highly recommended if you use them gaiters are recommended if you use them electrolytes are recommended if you use them insect repellant is recommended if the bugs are biting sunscreen is recommended if it's a sunny day something to sit on for lunch (recommended) On account of the terrain, this is not a beginner hike.
About Registering This is an application hike . As part of the registration process, the hike leaders screen potential participants with whom we have not previously hiked to ensure that you have the appropriate equipment and apparel as indicated above, and that your physical conditioning, skills, and experience are compatible with the requirements of the trip.
Please register in advance to secure your spot on this hike. The hike leaders will not accommodate participants who have not signed up and been confirmed for the hike.
When We Cancel Excessive cold or hot weather, steady rain, and possible thunderstorms/lightning will cancel the hike. Scattered showers will not cancel the hike.
Getting There Meeting spot, directions, and reminders will be e-mailed to confirmed participants prior to the hike.
Car pooling is always encouraged.
This hike is also accessible by MBTA (train) from North Station to the West Gloucester Railroad Station. Please inquire with the trip leader (jonathan.m.unger@protonmail.com) for scheduling information if you are interested in taking the train to and from the hike.
If you drive to the hike, there is a $2 parking fee.
Because of the limited size of the parking lot at the Tompson Street Reservation, we will be spotting cars in a larger off-site parking lot and carpooling to the trailhead as a group.
More information about the Tompson Street Reservation may be found on Greenbelt's website .
The Fine Print Sorry, no dogs; thanks for understanding.
We do understand that unforeseen circumstances beyond your control may arise, which may force you to cancel, if confirmed. Please consider your wanting to participate vs your being able to participate and your commitment to that participation before registering, and please don't be a No Show . If you do need to cancel, please do so through your AMC account/dashboard so that your spot can be filled in a hopefully timely manner, and please remember to mark your calendar so you don't become a No Show .
The hike leaders reserve the right to adjust the route if conditions warrant it (e.g. to avoid particularly slippery ledges if the trails are wet) and cannot guarantee the hike will be completed by any specific time.
Your Leaders For any questions, please contact the leaders!
Jon Unger (jonathan.m.unger@protonmail.com) Marjorie O'Malley (marjorieomalley@gmail.com)

Reminder: Please click the RSVP link above to register!