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How to Hike to a Brewery Outside of Boston

What are the hikes with the best views/destinations in the greater Boston area? Please tell me!

I’m always on the hunt for a good hike destination. Hiking to the top of a peak for a great view, like Great Blue Hill, or to a spectacular lake, like Mills Lake in Rocky Mountain National Park, there’s nothing like getting your sweat on, heart rate rising, working hard for a worthwhile payoff.

That’s why I was really excited when Widowmaker Brewing prepared to open adjacent to my favorite hiking area in the greater Boston area, Blue Hills Reservation. A unique hiking destination! I began planning my hiking route.

Photo: The group hike starting at Chickatawbut Tower (more strenuous)
Photo: Babywearing is encouraged at breweries!
Picture of relaxing hike in the Blue Hills Reservation

If you’re in the metro Boston area and want your next hike to include a stop at a great new brewery, here’s what you need to do:

Photo: Some parts are rocky and hilly.

  1. Check the hours of Widowmaker Brewing to make sure you’ll arrive when it’s open. How terrible it would be if you arrived and they were closed!

  2. Download the Blue Hills Trail Map and take a look at your route, with two routes described below.

  3. If you have a baby, pack your babywearing carrier-- this wike is more of a hike, not a walk, and it's definitely not stroller-friendly.

  4. Park your car at the reservoir on Chickatawbut Road in the Blue Hills (first route). There is a (very) small parking lot there. If it is full, you can easily park along Chickatawbut Road. If you’re looking for a longer and more strenuous hike, you can also park at Chickatawbut Tower and take the skyline trail until marker 3144, where you’ll pick up the directions below (second route).

  5. Walking at a brisk pace, the 1.4 mile hike to the brewery from the reservoir will take you about 30 minutes to complete (first route). This trail is mostly downhill, and it is rocky in parts. The hike back is a bit more strenuous, so don’t drink too much at the brewery! Follow the trail to marker 3131. Take a left onto Squamaug Notch Path until marker 3144, where you’ll curve and continue straight, crossing over the blue Skyline Trail. At 3143, there is somewhat of a rotary; you’ll take a slight left. At marker 3160, continue straight. At 3163, take a slight left.

  6. You’ll approach a fence. Follow the fence with it on your right until it opens up into a parking lot. Exit the path into the lot and continue to Wood Rd. (See photo)

  7. Take a right on Wood Road. I suggest crossing the road into the hotel parking lot, so you can stay off the busy street.

  8. Widowmaker Brewing will be on your left in the same building as the “Pure Hockey” sign. You'll see hops growing on the building-- so fun. Enter and enjoy!

Widowmaker has a nice beer selection (50 Year Storm was our favorite), and you can sample a few brews when you purchase a flight. They also have fun pub games and snacking foods like Cheeze-Its and Goldfish. You can purchase a hot dog and sometimes pizza. You'll often find food trucks visiting on weekends.

My favorite thing about breweries is that it is perfectly acceptable to bring your baby. They are judgment-free zones! Widowmaker is family friendly before 6pm as long as children are with their parents. We tuck our Inglesina portable high chair into our backpack along with some baby food and a bib. After arriving at the brewery and setting up, our wike baby is super happy, and mom and dad can relax and enjoy a drink before hiking back to the car.

This is a perfect way to spend a lazy weekend day—get outside together, take a wike, and grab a drink at a fun hiking destination. We’ve done it four times now and highly recommend it!

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If you try the brewery hike, let us know what you think!

Originally posted November 17, 2017; updated with revisions.

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