When Ethan and I moved to Acton, the Bruce Freeman Rail Trail was our very first biking adventure. The trail is beautiful, and runs ~12 miles from Concord to Lowell. Bikers, walkers, and runners welcome! The closest parking lot is the at the Bruce Freeman Trail lot on Concord Rd, Acton MA about 15 minutes away from the Boxboro Regency.
We love the hike up Old Indian/ Semuhenna Old Growth trail! A moderate, 4 mile round trip hike up to the 2K foot summit of Mt. Wachusett offers 360 degree views of the area. More on suggested trails and parking can be found here: https://www.mass.gov/doc/wachusett-recommended-hikes-and-rides/download And yes, we do sing Waaaa-wa-wa-chusett the whole way up.
This 1000-acre park features more than 20 miles of trails. You can see notable Native American sites and 17th-century cellar holes leftover from English settlers. There's also an active dairy farm that offers free tours on weekends. It costs $3 to park at Great Brook Farm
Ethan and I have been collecting wine glasses from Nashoba Valley Winery for about 2 years now. They have a great wine tasting menu, as well as some tasty cider & beer options! You sit back & relax, or take a stroll through the orchard grounds. But, be sure to save some space for the open bar :)
We haven't yet explored Oak Hill conservation land ourselves, but it appears that there is a perfect 3-mile, easy-moderate loop trail that peaks at the highest point in Littleton. Looks like a lovely, ~hour long nature walk with mild elevation gain. Only 10 minutes from the hotel!