Boston Rambles

Boston Rambles

A Rambler Walks and Talks About the Hub of the Universe

Best of the Upper Boston Post Road in Middlesex County, Massachusetts: A Top Ten List.

Abandoned section of the original Boston Post Road in Wayland, Massachusetts. All Photos taken by the author, this one on September 19, 2023.

This entry is self-explanatory: now that I have completed my walk along the route of the Upper Boston Post Road in Middlesex County, I want to list what I consider to be the most interesting sites along the road. I am doing this for many reasons: to reflect on the road that I have already covered and to celebrate the end of one section of this project; naturally, when I get through Worcester County I will do the same thing again and, eventually, post a list of the most interesting sites along the entire route of the Upper Boston Post Road. I also want to give readers a shorthand summary of what I have been doing thus far so that they do not have to read 100,000+ words to figure out what I consider the most important and relevant places to see along the road should they be interested in traveling it by foot (a great way to go), bike, or car. Finally, I want to mix up my approach to the entries in this project; most are long, detailed, and focus only on one town at a time but this entry will be short and comprised primarily of photographs with short captions. Anyone interested in more information can always click on the appropriate link to the specific town.

A quick summary: I consider this specific project, Walking the Upper Boston Post Road, to begin at the Watertown Bridge, 9.1 miles from the Old State House in Boston. Most of the other walks on this website are, with the notable exception of the entries from my previous project Walking the Post Road, which I am slowly transferring to this website, walks in the city, even if they are walks in Cambridge, Somerville, or Brookline, because they all link to each other at some point: These are walks in and around Boston. Once I headed west from Watertown Bridge the road leads away from Boston and does not link up with another road circling back to the city; the walks west are “traveling walks,” not “city walks.” I know this seems like an arbitrary decision but that is how I categorize the various walks.

Cambridge, Somerville, and Newton are all towns in Middlesex County through which I have walked and written about but again, they are part of my “city walks” and I do not consider them to be “traveling walks.”1I include in this list of “city walks” my walk from the border of Cambridge through Watertown to Watertown Square. Only the section of Watertown leading away from the bridge over the Charles at Watertown Square is considered in this admittedly quixotic list. Therefore the towns in “Middlesex County” for the purposes of this entry are as follows: Watertown,2From the bridge west as described in footnote 1 Waltham, Weston, Wayland, Sudbury, and Marlborough. Framingham, which is in Middlesex County and about which I have written an entry, is on the “Framingham Diversion” so it is not technically on the Boston Post Road. Therefore it does not get counted in this exercise (although, in truth, it will sneak into the list as you will discover). Southborough and Westborough, two more towns along the “Framingham Diversion” are in Worcester County, as is Northborough, the subject of the next entry in my Upper Boston Post Road Series. The distance of this section of the the project, from the bridge across the Charles River in Watertown to the border between Marlborough and the neighboring town of Northborough, the first town in Worcester County, is 25.0 miles.

To the list……

#10. Watertown Bridge, Watertown, Massachusetts.

Every time I cross this bridge it feels as though I am about to head off on an adventure. The place where the Upper Boston Post Road walk begins in my mind. A few yards away is the site of the Coolidge Tavern, where John Adams and the other members of the Massachusetts delegation to the Continental Congress dined before departing for Philadelphia on August 10, 1774: “The committee for the Congress took their departure from Boston, from Mr. Cushing’s house, and rode to Coolidge’s, where they dined in company with a large number of gentlemen, who went out and prepared an entertainment for them at that place. A most kindly and affectionate meeting we had, and about four in the afternoon we took our leave of them, amidst the kind wishes and fervent prayers of every man in the company for our health and success. This scene was truly affecting, beyond all description affecting.” Photo taken December 6, 2018.


#9. Union Common, Main Street, Marlborough, Massachusetts.

John Brown Bell, supposedly taken from the United States Arsenal at Harper’s Ferry, West Virginia, by Union troops from Marlborough, found its way here to Union Common, Marlborough, Massachusetts. Behind is the First Church of Marlborough. Main Street in Marlborough has a fascinating blend of historical artifacts covering more than three centuries of American history in a short span of less than half a mile. Well worth a wander. Photo taken February 26, 2021.


#8. Golden Ball Tavern, Weston, Massachusetts.

Golden Ball Tavern, Weston, Massachusetts. Great tour, lovely building, one of the best remaining links to the Boston Post Road from the Colonial era. Located in a lovely neighborhood along Boston Post Road in the center of Weston. Photo taken June 12, 2021.


#7. Hager Sawmill Site, Wayside Country Store, Hager Pond, Marlborough, Massachusetts.

Site of Hager Sawmill, Hager Pond, Marlborough, Massachusetts. Almost hidden from the passing drivers along Route 20 is Hager Pond, created by the dam that was used for the sawmill. Henry Ford moved a “country store” from Sudbury center and placed it next to the pond. Nearby is a short stretch of abandoned Boston Post Road in the woods and two 18th-century houses originally built for the Hager family. An incredible oasis of Post Road-related artifacts and natural beauty preserved in a desert of commercial development. Photo taken November 2, 2023.


#6 Training Field, Sudbury, Massachusetts.

Training Field, Sudbury, Massachusetts. The road leading past the training field near the Sudbury River in both Wayland and in Sudbury is the most bucolic area along the mostly busy and heavily-trafficked Upper Boston Post Road in Middlesex County. The scenery is lovely, the birding is great, and there is a poignancy about the scruffy, seemingly abandoned and easily-overlooked field, where militiamen mustered for battles from which some never returned, that makes this quiet section of the road, with views over the wide valley of the Sudbury River, one of my favorites. Photo taken May 30, 2023.


#5 Gore Estate, Waltham, Massachusetts.

Gore Estate, Waltham, Massachusetts. The most impressive building along the route of the Upper Boston Post Road in Middlesex County. A truly astonishing property to come across in the immediate suburbs west of Boston. How is this place not more well-known? Photo taken January 9, 2022.


#4 Old Town Bridge, Wayland, Massachusetts.

Old Town Bridge, Wayland, Massachusetts. This abandoned bridge across the beautiful Sudbury River is the most romantic spot along the route, hidden away from the noise and traffic of the main road; I startled a deer one day as I wandered across the bridge through thick overgrowth. Photo taken September 19, 2023.


#3 Crescent Street, Weston, Massachusetts.

At least a third of the original route of the Upper Boston Post Road is not on Route 20, which is the principal name of the road from Watertown Bridge to Northborough in Worcester County. Route 20 is often called Boston Post Road as it passes from town to town in Middlesex County, while the bypassed sections of the original Boston Post Road often have a different name. These little “forgotten” sections of the original road are often the most interesting parts of my journey and although always tranquil, often are packed with historical artifacts and usually have some of the oldest remaining houses along the road. These sections, to me, are closest to what the road might have felt like two or three centuries ago. This section of the old Boston Post Road in Weston, today called Crescent Street, is less than a mile from Interstate 95, yet parts of it feel unchanged since 1775. Photo taken May 20, 2022.


#2. Browne House, Watertown, Massachusetts.

Browne House, Watertown, Massachusetts. Another gem, one of the oldest extant houses (c. 1698) along the route of the Upper Boston Post Road. Historic New England offers superb tours of this truly incredible house. Photo taken June 3, 2017.


#1. Wayside inn, Sudbury, Massachusetts.

Wayside Inn, Sudbury, Massachusetts. A no-brainer. Personal connections (that’s my wife looking at the plaque commemorating the visit of the Marquis De Lafayette), a beautifully preserved (or maybe manicured) section of the original Boston Post Road that passes directly in front of the lovely inn and past the nearby chapel where we were married. How can I not pick this as my top site? Spend a night here after spending the day visiting all the other sites along the Upper Boston Post Road in Middlesex County, Massachusetts! Photo taken February 25, 2021.


Honorable Mention: Milestones, Wayland, Framingham, Southborough, Massachusetts.

19 Mile Stone, 1768, Wayland, Massachusetts. This stone, located in front of the Wayland Historical Society, was moved from its original location along the road leading to Framingham. This alternate road, which I have termed the “Framingham Diversion,” passed through Wayland, Framingham, Southborough, and Westborough, before rejoining the main road, the Upper Boston Post Road, in Northborough, as we shall see in the next entry of my Upper Boston Post Road series. The one thing the “Framingham Diversion” has that the Upper Boston Post Road does not have is milestones. There are milestones in Wayland, Framingham, Southborough, and even in Marlborough, while I found no milestones whatsoever along the route of the Upper Boston Post Road in Middlesex County from Watertown Bridge until I reached Northborough. This milestone is technically the right distance from Boston, but it is in the wrong place, so the honorable mention goes to the Framingham Diversion which has at least nine milestones. I will begin to discuss each milestone individually at some point in the near future when I begin my new series of short essays dedicated specifically to milestones. Photo taken February 27, 2019.

Enjoy the trip!3This entry was specifically written for a friend who enjoys “high-throughput” road trips! let’s see if this one makes it into the checklist!

One Response to Best of the Upper Boston Post Road in Middlesex County, Massachusetts: A Top Ten List.

  1. […] milestone along the route of the Upper Boston Post Road.10As I discussed in the last entry on Best of the Upper Boston Post Road in Middlesex County, the 19 mile stone in Wayland was moved to the Boston Post Road from the Framingham Road in the […]


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