Hiking by month
Hiking in MetroWest Massachusetts in May
Updated

Hiking in MetroWest Massachusetts in May is the reward for putting up with March. The trails are firm, the canopy closes over the course of the month, and there are more than fourteen hours of daylight to spend. It is also the month that tick checks become a nightly habit and turkey hunters are out at dawn, so a little planning goes a long way.
What May is like underfoot
The first week can still be wet in the low woods, but by the middle of the month most paths are dry and the streams have dropped. The leaves come out from the bottom up: shrubs first, then maples, then the oaks last. For a week or two the woodland floor gets full sun before the shade arrives, which is why the spring wildflowers all bloom at once.
Daylight runs from about fourteen hours at the start of May to fifteen by the end, with sunset after 8 PM in the last week. Timeanddate's Boston page has the exact times.
Memorial Day weekend is the switch. DCR starts charging for parking at Hopkinton State Park that weekend, the guarded swimming beaches open in late May, and the summit road at Wachusett opens to cars. Before the holiday, the same places are quiet and free.
Hiking in MetroWest Massachusetts in May: where to go
Garden in the Woods at its best
Garden in the Woods in Framingham, 20 to 25 minutes from Southborough, is Native Plant Trust's 45-acre botanic garden with more than 1,000 species of New England native plants. The main route is a mile-long crushed-gravel loop that takes an hour to an hour and a half, with a steep slope at the entrance. Early and mid-May is the peak for the woodland wildflowers that flower before the trees leaf out. Admission is charged, dogs are not allowed, and the lot holds 42 cars, so a large group should carpool and arrive at opening.
Chestnut Hill Farm and the bobolinks
Chestnut Hill Farm in Southborough is a 170-acre working farm owned by The Trustees, free and open daily from sunrise to sunset. Its two miles of easy trail cross hay fields and pasture into oak and pine woods. The Trustees keep designated bird reserves in the fields for bobolinks and eastern meadowlarks, both of which nest on the ground from late spring. Stay on the marked trails, assume every electric fence is on, and leave the dog at home: they are not permitted here.
The Sudbury Reservoir Trail
The Sudbury Reservoir Trail runs about five miles along the shore across Southborough. Shoreline fishing has been open since the first Saturday of April, so expect anglers at the usual spots on weekend mornings. Swans and other waterbirds are on nests along the shore; give them a wide berth. DCR's public access rules for the watershed land prohibit dogs, bikes, swimming and any contact with the water.
Turtles at Broadmoor
Mass Audubon's Broadmoor in Natick, about 30 minutes east, has eight miles of trails along the Charles River. Mass Audubon says turtle watching is a favorite from late spring on, with painted turtles basking among the lily pads. Trails are open Tuesday to Sunday and Monday holidays, dawn to dusk. Non-members pay admission and dogs are not allowed.
A summit before the crowds
Wachusett Mountain State Reservation in Princeton, 45 to 50 minutes away, has 17 miles of trails to a 2,006-foot summit. Until Memorial Day weekend the summit road is closed to cars, which keeps the top quiet for anyone who walks up. After that, DCR charges for parking and warns that the visitor center lot has only 28 spaces.
Drive times are approximate, from Southborough town center, and vary with traffic, especially on Route 9 and the Mass Pike.
Turkey season and ticks
Spring turkey season runs from late April into the fourth week of May. In 2026 the MassWildlife season summary lists April 27 to May 23; the dates shift slightly each year. Turkey hunters are out at first light, in camouflage, on most state forest land and by DCR permit on the Sudbury watershed. There is no hunting on Sundays in Massachusetts. MassWildlife's advice for non-hunters is to wear something bright orange, avoid earth tones, and talk or whistle so you are known to be a person. Breakneck Hill and Beals Preserve do not allow hunting at all.
By May the poppy-seed-sized nymph deer ticks are out as well as the adults. The state's tick guidance is plain: stay in the center of the trail, wear light-colored long trousers tucked into socks, use DEET on skin or permethrin on clothes, and check everyone once a day.
Back at the house
The garden at Southborough Garden Retreat is in full leaf by mid-May, the pond is loud with frogs, and the patio under the string lights is the right place to compare tick checks. Jillian, the host, can point you to the walks in best condition that week, and our garden lovers' guide covers the gardens worth a day.
Neighbouring months: April and June. For the whole season, see the spring outdoors overview.
Useful links
- Native Plant Trust: Garden in the Woods
- The Trustees: Chestnut Hill Farm
- Town of Southborough: Sudbury Reservoir Trail
- DCR: Sudbury Reservoir rules
- Mass Audubon: Broadmoor, Natick
- DCR: Hopkinton State Park
- DCR: Wachusett Mountain State Reservation
- MassWildlife: 2026 hunting season summary
- MassWildlife: safety tips for non-hunters
- Mass. Department of Public Health: tick-borne disease prevention
Bringing a group?
Southborough Garden Retreat sleeps fourteen, with a library, a glass plant room, a projector room, a gym and an acre of garden. It is a Guest Favorite on Airbnb, rated 4.95.
See the houseMore guides

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