As you drive west of Boston, the towns become more wooded with historic homes and small farms. Hopkinton & Holliston are two of these towns that are easily commutable to Boston but still have the charm of small town life. One way to explore these towns is just to drive around the windy, narrow roads and enjoy the historic farm houses, small cemeteries, and countless stone walls.  However, if you want some more direction on where to go, here are some highlights.

Located 26 miles west of Boston, Hopkinton is best known for being the start of the Boston Marathon – the nation’s oldest annual running race. Every Patriots Day, over 25,000 runners make their way out to Hopkinton to start their race. To find the start line, look for the statue honoring “The Starter”, Hopkinton resident George Brown who served as the starter for over 20 years, at the Hopkinton Town Common.  This isn’t the only statue in honor of the annual race: outside of the Center School is the “Yes You Can!” statue, a tribute to the Team Hoyt, a father son team who competed in 30 marathons; and next to Weston Nurseries – the one mile mark for the race – is “The Spirit of the Marathon”, a statue of Spyridon Louis (first Olympic marathon winner) and Styliano Kyriakides (1946 Boston Marathon winner).  

The race also inspired the name for Start Line Brewery.  The brewery boasts a large selection of beers on tap, a full food menu for lunch and dinner, both indoor and outdoor seating, and merchandise and beer to go.  It’s a nice way to spend an afternoon or a night out; they have trivia Wednesday nights and live music Thursday nights. 

Weston Nurseries (next to “The Spirit of the Marathon” statue) is worth a stop to browse for those plant lovers in your life or to appreciate the designed landscapes featured outside and the plant displays featured inside.  They often have food trucks on site during the warmer months, and there is even a model train set built around a small pond behind the main building to watch.

To appreciate nature in the raw, head over to Hopkinton State Park.  The park is set around a good size lake, which allows for swimming & picnicking.This park has boat rentals (canoes, kayaks, and sailboats) to take out and explore the few islands and far reaching banks of the lake.  There are also some hiking trails that take you into the wooded side of the park. 

For an easier walk, head over to the Holliston Rail Trail. As the name implies, this walking and biking trail was created on the path of an old railroad route.  Made of packed stone, this section of the rail trail  (it is part of the longer Upper Charles Rail Trail that connects Sherborn, Holliston and Milford) makes for a nice walk or jog. If you park at Blair Square, it is a 1 mile walk to the Philips Tunnel. Along the way, there are benches to rest and plaques to learn about the history of Holliston.

One of those plaques talks about “Casey at the Bat”. This 1888 poem by Ernest Thayer focuses on a fictional baseball team from Mudville.  Mudville was the nickname for this area of Holliston, where Irish immigrants working at the nearby factories lived. The Mudville neighborhood is worth a walk around. Because the houses originally belonged to factory workers, they are small and close together. However, you can tell there is a strong sense of community here as the houses are all well kept with cute gardens, little free libraries, and designated sitting areas. Set within this neighborhood is a statue in honor of the poem & a memorial in honor of the Irish immigrants who settled the area. 

If you happen to visit Holliston during one of Waushakum Live Steamers public events, make sure to check them out.  Set in the middle of the woods at the end of a neighborhood street, you would never know this place existed. A few times a year this steam locomotion train club opens its space to the public for train rides through the forest. They also have members around to talk to you about the maintenance and running of the trains and the track. 

While in Holliston, be sure to stop by one the farm stands for local produce, plants, and food: Outpost Farms, Arcadian Farms or MacArthur Farm. 

Google Maps of places mentioned in this post