The Idea

I may be biased, being from there and all, but New England is a unique region. As far as I know, it’s the only officially defined region in the country. Six states: Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

So as a cyclist who always thinks he can do more than he probably reasonably can, the natural question is: How fast can I hit all six states? Or, more realistically, can I plan a trip to hit all six and actually make it happen? (Spoiler: If you can talk a friend into driving a sag wagon, it makes things a lot easier.)

After years of discussion, mapping out routes, and wanting to but not actually doing the trip, this year my brother Andy and I finally did it. Our routes factored in direct travel, bike-friendly roads (from what we could tell from Strava and Google Maps) and, to have some non-arbitrary waypoints, various places from our childhood and family history.

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Day 1: Manchester NH to Auburn MA

70 miles, 3,100 ft. Elevation

The grand départ was our friend Big Dave’s house in Manchester. Grand plans of having Big Dave drive Andy’s converted adventure van — along with spare gear, supplies, and Andy’s elderly dog — fell through as soon Big Dave tried to fit in the cab. We urgently pared down our stuff and fit it all into his Bronco instead.

We rode a nice bike path from southern NH into Ayer, MA, and then wound our way towards Worcester, the second biggest city in New England. We made our way through the city in what was our only stretch of urban riding and nearly followed our GPS route onto a highway before noticing a local exit in the interchange, which brought us eventually to our hotel in Auburn and a hearty meal at an Applebee’s.

The only point of family history on this leg was one that we missed: the former site of a Ground Round restaurant, where we used to stop as a family when driving between southeastern NH and northwestern CT, and where I remembered the projector screens showing old movies and the Slider Sundaes that came in little plastic MLB helmets that we collected.

The site of the restaurant – if we even did our internet sleuthing right – was right by a traffic circle in north Worcester, and we blew right by it and didn’t feel like going back through the traffic when we realized it, just for a picture of a business park.

Day 2: Auburn MA to Monterey MA via RI and CT

124 miles, 10,200 ft. elevation

We ducked onto some backroads pretty quickly, and cut the northwestern corner of RI into CT to hit 4 of the 6 New England states, all before lunch on just the second day. It wasn’t much of a tour through the Ocean State, but at least the roads were good, the air was cool, and there was no traffic. Soon after we exited RI into CT, we stopped to refill our bottles from Big Dave’s Bronco at the trailhead for a rail trail, where I also swapped out my road wheels to my spare set with my 32mm gravel tires.

Rail trails, for those not aware, are recreational paths that are repurposed from old rail lines. These may be paved or not, and they are not hard to find in New England.

Rain was threatening but it held off, and we wound up with a Strava Top 10 or two on the trail, which was a nice surprise at the end of the day. We cut along the northern part of CT, across its eponymous river, and into Southwick MA where we had lunch as drizzle fell at the Summer House, another restaurant we’d stop at as a family in our travels between CT and NH.

The latter part of the day featured some mild rain as we curled up, around, and down the many hills of western MA. We dried off for the most part as we were approaching our destination, the small town of Monterey. We figured we could take a shortcut from the planned route and avoid yet another climb and a dirt road (I had my road wheels back on, at this point). Naturally, it wasn’t a shortcut after all. We looped around Monterey and added another 5 miles or so to our long day’s tally.

Old family friends live here. We cleaned up, had a great dinner with them, and caught up on the many years that had passed since our last visit (well, for me at least, Andy had stayed here a few years back on another cycling excursion).

Day 3: Monterey MA to Norfolk CT

18 miles, 1,600 ft. elevation

The forecast did not bode well, but at least today was very short. We timed our ride south to Norfolk CT, and arrived dry. We had lived here until I was three and Andy was eight, and we usually came back in the summers after we moved to NH.

We did a quick tour of the scenes of our youth in Norfolk: through the Yale summer music school campus, by the town green and behind the library, past the liquor store where we turned in aluminum cans we gathered for the five-cent deposits, and up the hill past our old house.

We skirted some environmental cleanup from a gas truck that had tipped over a few months back and then stashed our bikes under a deck at the home of more old friends of the family as the rain came down. It started coming down hard.

This effective rest day was welcome, but we had a long day following, and the weather didn’t look promising. We didn’t have the time to wait out the rain for a day or two, and I had the deflating possibility of abandoning the ride in the back of my mind. We just had to hope and wait.

More good meals, rest, and device charging ensued. I should have done laundry but somehow didn’t think of it.

Day 4: Norfolk CT to Brattleboro VT

105 miles, 4,200 ft. elevation

We weren’t going to avoid the rain, but it didn’t seem bad enough to bail on the trip, or force a major reroute. There was no thunder or lightning on the radar at least, so we set off around 9:30 AM, a bit later than we originally planned.

Our original goal was to go north through MA into VT, where we’d give The Green Mountain state the same perfunctory corner-cutting treatment we gave RI, and then finish in Keene, NH. With the weather, there was a good chance it wouldn’t happen.

It was a wet day, and what turned out to be the first day of torrential flooding to hit VT in mid-July. We both started out with shoe covers on and took them off when we optimistically thought we’d caught some clear skies about 20 miles in. The precipitation was never very hard, but the roads were wet enough to soak you even if it wasn’t raining at the moment. The nice thing about getting soaked was that we couldn’t get any wetter, so we just soldiered on.

I had switched to my gravel tires, which were slower, but the extra width and tread felt reassuring. The water on the roads made sure we couldn’t let loose on the descents, but we at least got some beautiful views of farm country with fog rising off the green hills.

We called an audible and decided to stop in Brattleboro instead of Keene NH (still most of our planned route). On top of being tired, wet, and getting a later start than we wanted, the section of our route that we were cutting out was mostly dirt, and mostly hilly, and those were two things we didn’t want to attempt to deal with following or during heavy rain.

After running into construction detours and pedaling through two feet of water in a cemetery, we made it downtown to a strip mall parking lot, our day’s finish line. Amazingly, we managed to fit three humans, the shortest of whom (me) was six feet tall, into a Big Dave’s convertible Ford Bronco along with two bikes, a spare set of wheels, a 17-year-old Yorkie, and probably a dozen bags of clothes, gear, and supplies.

We checked into our hotel in Keene, where Big Dave and Andy had met in their early college years, ate a bunch of food at an understaffed but tasty pub, and cleaned our bikes in the hotel shower.

Day 5: Keene NH to Exeter NH

88 miles, 4,500 ft. elevation

We began the morning with a tour of the Keene State campus to compare it to Andy’s school memories. I think the consensus was that everything looked smaller after a couple of decades. Jumping benches came up in both Andy’s and Big Dave’s college stories; not sure why. 

Andy had some considerable brake rub right before we went up a dirt road climb outside of Keene, and we lost some time adjusting the caliper. This was probably the worst mechanical issue we had, so not too bad in the grand scheme of things.

The day’s primary destination, other than the finish, was a coffee shop in Goffstown where our father and his cousins were meeting us. Serpentine lakeside roads brought us there, and we were both confused at first to see rafts and docks submerged, with weights holding them under the surface. There had been so much rain that the lakes had swelled, and we learned the rising water threatened to de-anchor these.

We got lost a couple of times, following the erroneous GPS route too faithfully. Andy won an argument that eventually put us back on course. We passed towns too quaint to seem real and went through one of New England’s famous covered bridges. Coffee and snacks (and leftover pizza from the pub in Keene) refueled us in Goffstown and we got to catch up with our relatives who had come out to cheer us on.

It was almost entirely rail trail onward to Manchester, in central NH, and then again from there towards Exeter. We made great time on the well-graded and mostly well-maintained dirt and gravel and rolled up to our parents’ house before dinner time.

Day 6: Exeter NH to York ME

33 miles, 1,300 ft. elevation

Day six was really day seven if you count the full rest day we took. We were both gassed from 400 miles and about 20,000 of climbing over the previous five days and not riding for a day was what our bodies needed.

We had only one state left, and after catching up on some work, we set out for ME and our mountain-top finish. Most of the ride was on familiar roads, both from growing up in the area and cycling in more recent years when we visit in the summer.

We got perhaps our first meaningful tailwind of the entire tour and rode it most of the way to the base of Mt. Agamenticus. It is not a tall mountain, and the road to the top is not long, but it is steep: over 10% for about a kilometer. I’d never done it before and figured I’d hammer it for all I got. I got confused about where to go at the very top (I went the wrong way into a parking lot exit) but still made it in just under four minutes.

Cresting the top of Mt. A., as it’s known, you look east across the Atlantic. The sun setting behind me cast all sorts of colors into the sky above the ocean, a nice surprise for me as I was huffing up the final hump. Andy and I drank it in for a bit, rode around to make the most of the views, and snapped some pictures. Our dad was waiting in his car so we loaded up our bikes and that wrapped our tough but beautiful Tour de New England.

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Our Gear

Me: 

[product-block handle="7506456936640-specialized-roubaix-comp-road-bike-2020-56cm"/]

• 2020 Specialized Roubaix Comp

[product-block handle="7497909305536-zipp-302-disc-carbon-clincher-700c-wheelset"/]

[product-block handle="7392020201664-continental-grand-prix-5000-tire-700c-x-25mm-330tpi-clincher-black"/]

• ZIPP 302
• 25mm Continental GP5000 tires

[product-block handle="7499966644416-dt-swiss-r470-aluminum-tubeless-700c-wheelset"/]

[product-block handle="panaracer-gravelking-ss-tire-700c-clincher-black-brown"/]

• DT Swiss R 470 db
• 32mm Panaracer GravelKing SS tires

Andy: 

[product-block handle="giant-revolt-advanced-3-gravel-bike-2021-large"/]

• 2018 Giant Revolt 
• 35mm Compass Jon Bon Pass tires

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