Milford and Holliston. December 4, 2022

Day/Date:  SATURDAY -12/4/22
Towns visited: Milford & Holliston
Had we ever been to these town before?  No
Drive to 1st town:  26 miles    Time spent in town(s):   5 1/2 hours

What did we do in the town/area?  

It’s a great feeling to walk into a new business owned by two cool women who have made it their mission to serve up coffee and community. Blooming Hearts Coffee Roasters, a reasonably new cafe and coffee roaster in the Nathaniel Plaza in Milford, was the perfect place to start our day. They opened less than six months ago, and you can tell that people love it! It has a welcoming and comfortable atmosphere, and we were pleased with our lattes! 

And to add to the yumminess, the next store over was Basic Batch Donuts, a “from scratch” bakery with some pretty fun and delicious-looking donuts. We’re talking donut flavors like “Fruity Pebbles,” “Maple bacon,” Cranberry cheesecake,” and “Butter cookie.” They looked and sounded so good that although we weren’t hungry at the moment, we couldn’t resist buying a couple to take home (and to share with family). 

After all of that deliciousness, we decided a nice walk along the Milford Upper Charles Rail Trail was in order. We parked at the Cedar Swamp pond and walked towards Louisa Lake. The trail is mostly paved, but a couple of off-shoots by the lake granted us some views of the lake and a beautiful swan gliding along the water.

After our walk, we drove through the downtown area, completely missing the hard-to-miss town hall. We had to turn around. We laughed when we finally saw it because it’s beautiful and grand and unlike the other buildings nearby and we really shouldn’t have missed it. 

Lastly, we stopped at the Historic old St Mary’s Cemetery to see a round Irish tower we had read about. It is believed that there is none other like it in the U.S. Built in 1896, a local Irish parish priest intended this tower to be like the watch towers of Ireland.

It had a striking and unique presence.


Just 6 miles from our last stop in Milford was the first stop in Holliston: the Town Hall. Another pretty building next to a New England-y painted white church amidst the downtown area. We parked the car and walked down to Fiske’s General Store. This store has been in existence since 1863, and it feels like there is something for everyone inside. There were handwritten signs everywhere promoting everything from made-to-order Holiday Bows to Pokemon cards. The assortment of inventory included: cards and gifts, candy and crafts, games and housewares, holiday fare, a squealing pink rubber chicken dressed as Santa, and more. It was fun to shop around, and we walked away with a sweet little tree for our mantle and a few holiday gifts. One of the owners showed us an x marked on the carpet, telling us that this was the very spot where he met his wonderful wife 50 years ago (she was right behind us and glanced over with a smile). 

Hungry and ready for lunch, we crossed the street to the Superette, where we waited in line to order a homemade sandwich for lunch. After gobbling those up, we drove to the site of the old, lost site Darling Woolen Mill just across the street from the 8 arch bridge; a recently restored bridge incorporated into the Holliston portion of the Upper Charles Rail trail, and that is where we headed next. 

Just off the rail trail (and just past the post with W, aka-whistle post), was the entry to the Wennakeening Woods where we made a 3/4 mile long loop trail in the woodlands.

Historically, a whistle post means to inform the train conductor to blow the train’s whistle so as to warn anyone in or near the crossing that the train is coming.

Then we headed to the “Open House” at the Historical Society’s Asa Whiting house.

We felt a little out of place here as there were many people mingling who clearly all knew each other there, but the house was filled with artifacts & toys on display from many different decades from the turn of the century to the 1970s. We enjoyed some hot apple cider and noticed a portrait of Dr. Timothy Fiske, the first trained physician in Holliston. It turns out it was his grandson, James Ferdinand Fiske, who founded the Fiske General Store that we visited earlier! It was a fitting way to end the day.

Indigenous/ Native land info for this region: Nipmuc

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