A hike twenty minutes north of Boston can feel like the middle of New Hampshire woods, if you know where to look. On an unseasonably warm February day, we combined these hops: Lord Hobo Brewing Co. beer with this trail: the Middlesex Fells Reservation in Winchester, Massachusetts. Here’s what we’d recommend for a full day plan.
The Trail
Even in the middle of a snowy winter, the Middlesex Fells trails are passable since they’re highly trafficked by human and four-legged pedestrians alike. Our pick on one such snowy day was doing half of the Skyline Trail – a five and a half hour loop that can be shortened to 4 hours easily.
Start at Long Pond parking and hop on the trail for a few hours before finishing up on the Cross Fells Trail.
The Hops
Bring a beer in tow on your hike to celebrate when you finally catch a glimpse of the Boston skyline – our pick was Lord Hobo Brewing Co. Boomsauce.

Follow up your hike with a visit to the Lord Hobo brewery around the corner from the Fells in Woburn. Dubbed “their modest castle,” you’ll be pleasantly surprised with free flights, giant Jenga, and cheap growlers.
Really outdo yourself by ending the day with dinner at Border Cafe in Burlington.
