My Route


I must admit there wasn’t a lot of fore thought and planning  when I started my hike across Massachusetts back on June 17. I worried if I planned too much or told too many people about it I’d never get started. I was afraid of failure and disappointing people if I suddenly quit because I wasn’t up to the challenge. And since it’s a sectional hike, I figured I had five days each week between hikes to plan it as I go along.

I did contact BJ Hill for advice, a Spencer, Mass. resident, who has walked across Massachusetts twice and the entirety of the continental United States.

BJ Hill & Me

He knew a little something, something about what I was doing. I also consulted paper and electronic maps constantly for possible routes across the state, and in the end I decided on using Google Maps walking feature. I entered starting and end points over and over carefully reviewing each segment looking for anything that would keep me away from heavily trafficked roadways with speed limits of 50 miles per hour or greater. Sometimes this involved taking longer routes but it was better then a stream of cars or 18-wheelers breathing down my neck.

The problem with my strategy was that it didn’t allow much time to stop, reflect, and see things because I was constantly on the move. If I stopped frequently my walks turned into 8-9-10 hour days depending on how far I was hiking.

When I first started, a 12 mile walk took about 6.5 hours. As I near the final 42 miles it now only takes about 4.5 hours to cover the same distance depending on the weather and temperature. A recent 20 mile walk from Bridgewater to Plymouth took eight hours. During this time I might pass through two or three towns before reaching my final destination for the day.

I’ve been fortunate in that I have had nine to ten straight weekends of good walking weather this summer here in New England. Tropical storm Jose delayed my finish about a week in mid-September.

Here is my route, mileage and itinerary. Keep reading for updates as I cross the state.  I hope to see you on the road!

“The first step towards getting somewhere is to decide that you are not going to stay where you are.” John Pierpont Morgan


Day 1: Saturday June 17. I started in Petersburg, NY along the Taconic Trail before quickly crossing over into Williamstown, to begin the journey on Route 2 to North Adams (15.97miles). Because I didn’t have a ride to the starting point I ended up walking about three to four miles up the Taconic Trail (No Uber in Williamstown) before a Scout leader saw me and gave me a ride to the top of the mountain where I entered Williamstown, Massachusetts.


Day 2: Sunday June 18. North Adams, Adams, Ashuwillticook Rail Trail, Cheshire. (12 miles)

Day 3: Saturday June 24. Cheshire, Lanesborough, Dalton to Hinsdale (13.06 miles)

Day 4: Sunday July 2. Following the scenic Route 143 from Hinsdale I quickly crossed over the western up ledge into Peru and continued along this route until Lindsay Road in West Worthington. I turned right onto Lindsay Road and feel in love with one of the most scenic roads in the state. I continued to follow it until it turned into Buffington Hill Road to Worthington Corners. I continued on Route 143 up a monstrous hill into West Chesterfield and Chesterfield ending at Stage Road. (15.78 miles)

Day 5: Saturday July 8. Chesterfield to Amherst (23 miles). Longest walking day of the entire hike. It took approximately 9 hours to complete this segment.

Day 6: Sunday July 9. Amherst to Belchertown (Quabbin Reservoir) via Old Bay Road and Route 9,  Short walk due to high heat and sweat pouring into my eyes. (8 miles). Traffic along this stretch of Route 9 really unnerved me because there was very little shoulder on the roadway after crossing over Rt. 202 towards the Quabbin. Traffic can be constant and steady in both direction on this scenic, cross state road.


Day 7: Saturday July 15. Belchertown (Quabbin Reservoir Visitors Center), Ware, West Brookfield via Route 9. What was most memorable about this hike was getting stopped by a West Brookfield Police officer who told me hitchhiking wasn’t allow in the town. Then I asked the officer how did he recommend I get back to the Quabbin Reservoir? He said “you better start hoofing it.” I ultimately received a ride from a passerby who read my sign, “Quabbin Reservoir,” and offered me a ride.  Fortunately I had no other incidents with police anywhere else in the state. (13.55 miles)

Day 8: Sunday July 16. West Brookfield, Brookfield, East Brookfield, Sturbridge, to Charlton Public Library. It was along this walk that I began to feel like I was hitting the edge of metropolitan Boston. The houses became closer, traffic increased on small two lane roads, and more and more American flags started to appear in the front of houses. Additionally, the landscape started to change along this stretch of the trip. This was one of the more beautiful journeys on my hike. It involved heading east on Route 9 to Quaboag St., Shore Road and onto the fashionable Podunk Road. For weeks after I told people “There’s nothing Podunk about Podunk Road.” (12.88 miles)

Day 9: Saturday July 22. Charlton, via Mid-State Trail, to Oxford (8.58 miles). It was along this stretch of the Mid-State Trail that I almost lost my shoe in thick mud, discovered what a cow pass was, and encountered lovely historic villages on this hike.

Day 10: Sunday July 23. Oxford, via Mid-State Trail, to Douglas State Forest (13.28 miles). I was joined on this walk by my friend Michael Richardson from Boise.

Day 11: Saturday July 29. Douglas State Forest to Purgatory Chasm (Sutton), Northbridge, Whitinsville, Blackstone River & Canal Heritage State Park, Uxbridge. A fun hike to see the glacial boulders at the Purgatory Chasm. (18.77 miles)

Day 12: Sunday July 30. Uxbridge to Mendon. A short hiking day. I loved walking along the Blackstone River canal towpath for the ever so brief 3/4 of a mile. (5.79 miles)


Day 13: Sunday August 6. Mendon, Bellingham, Franklin, to Wrentham. I discovered the Town of Franklin was Horace Mann’s birth place. Mendon and Franklin were probably the most scenic towns of this walk. (14.22 miles)

Day 14: Saturday August 12. Wrentham, Foxborough, North Easton (14.49 miles) Easton is a town worth exploring more. Some interesting state forests in this area that I would like to return to see.

Day 15: Sunday August 13. North Easton, Easton, West Bridgewater, Bridgewater (10.22 miles). Bridgewater is interesting with the state college located there. The center of town, with stores ringing the common, make it a nice brief walk. There wasn’t a whole lot of activity going on when I started out walking from there early one Sunday morning.

Day 16: Saturday August 19. Bridgewater, Halifax, Plympton, Plymouth, to Plymouth Rock (20.67 miles). This was a very lovely walk after getting past Halifax. I loved the open fields and farms of Plympton. Plymouth is center point of many of the towns in this region. I was ecstatic about reaching Plymouth because it marked the boundary of the state for me when I reached the Atlantic Ocean. Fun, historic, tourist town, lots of restaurants and shops to browse.

Day 17: Sunday August 20. Plymouth, Cedarville, Bourne, Sagamore Beach (14.96 miles)


Day 18: Saturday August 26. Sagamore, Sandwich, to West Barnstable (11.26 miles)

Day 19: Sunday August 27. Barnstable, Yarmouth, South Dennis, to Cape Cod Rail Trail (13.53 miles)

Day 20: Saturday September 9. Cape Cod Rail Trail, Harwich, Brewster, Nickerson State Park

Day 21: Sunday September 10. Cape Cod Rail Trail, Orleans, Eastham, Wellfleet, MA

Day 22: Saturday September 16. Wellfleet, Truro, Provincetown

Day 23: Sunday September 17. Race Point Light House, to dip my feet into the Atlantic Ocean





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