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  • Writer's pictureAndy

Flyover Space: A Ride Through Middle Massachusets

The rain wouldn’t quit. What I thought had been a passing burst- given its intensity- wouldn’t relent. It poured and poured. I had waited it out as long as I could, but I needed to make distance before nightfall and it was time to dive in. It took minutes for me to get soaked to the bone and for the second time that day I was waterlogged. The trail I was on had also deteriorated into a streambed. Water was rolling in waves as I pedaled upward trying to avoid the deepest eddies. What luck. The hardest rain of the year and I was out in it. And that’s when it hit me.

Almost exactly twenty four hours earlier I rolled off the MBTA commuter rail at Wachusett Station in Westminster, MA with my bikepacking gear and a plan to explore an often overlooked corner of Massachusetts. I know this is a recurring theme here, but I was again on my way to find adventure in an unheralded locale. Usually when people think of outdoor adventures in Massachusetts they are talking about the Cape or the Berkshires, not Baldwinville or Orange. America has flyover states. Massachusetts has Gardner, Winchendon and Templeton. The genesis for my adventure in Central Mass started on one of my first bikepack trips from Boston to Northampton. I had ridden several sections of the Midstate Trail, and been thoroughly beat down by it. So of course I needed to go back for more. And a return to the heart of darkness is where my journey would begin. The miles of Midstate just north of Wachusett Station had nearly broken me on my last visit, but this time I was headed in the opposition direction. My hope was that this would change the quality of the experience.

Thankfully, fresh legs and the change of direction did the trick. The steep wooded singletrack that I had spent hours climbing on my last visit were a joy to descend. And the climbs in the opposite direction were gradual and manageable. With the exception of one short hike-a-bike section, the first few miles breezed by. At the height of land there was a large farm and the trail followed a rock wall on the edge of the field. A group of boyscouts were setting up in a young grove of trees overlooking Crocker Pond. I wound my way through the troupe and started my first descent of the day through an old hardwood stand. I passed behind houses in a suburban neighborhood and emerged onto a road where I started a steep paved climb. Doubletrack awaited as I entered woods again and made my way to Mud Pond- a highlight of my previous trip- where a lean-to sits in a picturesque stand of pines aside a large pond. As it was late May, tick season was in full swing and I had already swiped four from my legs in just a few short hours on trail.

I had been feeling “off” the whole morning, and despite having not traveled very far, I started to get very comfortable with the idea of settling down for the night at Mud Pond. I set up my hammock between some trees as a small group of swimmers arrived. Simultaneously another biker and hiker arrived from opposite directions, with gear to set up camp for the night. What had been a solitary retreat quickly became a busy hub of activity.

The swimmers eventually continued on their way and just the hiker and biker remained. I learned they knew each other and had planned to meet at the lean-to for a night of camping. Where I had brought a spartan dinner of spiced couscous they had an extravagant spread of chicken and sausages which they eagerly shared. As we sat around the campfire that night we traded stories of our adventures, and soaked in a beautiful summer night. I slept soundly and when I awoke rain was threatening. I quickly packed up, bid my new friends goodbye, and continued north on the Midstate. I knew a long descent awaited and I was not disappointed as the next two miles were a fast and fun descent to the road below. On the far side of the road, drops of rain started to fall as I started my climb. The trail was steep but beautiful. It wound upward alongside a small brook and then followed a stone wall dividing a fern blanketed forest. I crested a steep rocky climb with an overlook to Stodge Meadow Pond just as the rain picked up. With all the ferns, my tick count had now doubled to eight.

Although sweaty, I was still relatively dry in my rain shell as I descended down to Winnekeag Lake. I zipped along some well traveled trails along the lake and started climbing again into the forest. The trails eventually reached Ashburnham State Forest, where I descended through a gorgeous stand of evergreens to a dirt road below. The road led me past countless summer camps along Lake Watatic and Sunset Lake. I had not seen a single soul on trail all morning, and the route might as well have been in northern New England for all the solitude it provided. What few people enjoyed this area, were likely safe and dry in their camps- hiding from the now driving rain.

The paved North Central Pathway welcomed me on the far side of the lakes just as the steady rain became a downpour. While I appreciated getting off-road again, I longed for the shelter of wooded singletrack as I raced along the pavement into Winchendon. A stand of event tents in the grassy field behind the YMCA on the edge of town offered shelter as the downpour persisted. I decided to sit tight for a while and broke out my stove for some coffee to warm up. It was just me, my hot coffee, and the ticks. I was now up to a dozen.

Before long it became apparent that the passing downpour I was enjoying wasn’t letting up anytime soon. And so I spied a local pizza restaurant and pedaled over for some food, shelter and warmth. One and a half hours, one pizza, and the slowest-ever trip to Rite-Aid later, I was back into the deluge, which hadn’t eased in the slightest.

Having no idea what to expect, I was pleasantly surprised when I hooked up with the Ware River Rail Trail on the western end of town and discovered an unpaved, unkempt “corridor”- unlike the bike highway that had taken me into Winchendon.

Rain thundered down onto the leaves above me as I rolled west and then south on the trail. The occasional mud pit slowed my progress, but for the most part there was passable singletrack along the old rail line. And then suddenly, it deteriorated into a streambed. As I looked ahead I could see a beaver pond overflowing onto the trail and then rolling down toward me like some wide rain fueled brook. And that is when it hit me. I had every right to be miserable. Angry even. But I wasn’t. Amidst all the awful conditions were all the intertwined joys. I was soaking it all in: the verdant greens, the clean crisp smell of fresh rain, and the thundering sound of rain on millions of leaves. Sorry Gump, but life is like a ribeye steak. Sinew and muscle marbled with the good stuff. I realized that if I was focused on the bad, that is all I would see. And so my eyes opened to the beauty of my situation, and with renewed enthusiasm and resolve, I pushed onward. The rail line eventually reached Baldwinville, where I had to jump onto road until finding trail again on the far side of town. The trail was much better maintained as I continued south toward Templeton State Forest. I resolved to try and find a cabin at one of the campgrounds that I knew waited just beyond the state forest.

A deer leaped through the swamp as a turtle scampered across the sandy trail at my feet. I was only a few hundred yards from the hum of Route 2, but I was surrounded by wilderness. Emerging the from trail onto the paved road, I went in search of a dry room for the night. All the cabins were taken at Peaceful Pines, and when I arrived at Lamb City the office was closed as it was a Sunday afternoon. It was looking like I might need to tent it for the night but there was still one option left, and so I rolled up to the King Phillip Motel and Restaurant. Looking like a drowned rat, I wandered into the bar and asked if they had any rooms, and was somewhat astonished they didn’t immediately dismiss me. After a shower and some dry clothes I made my way back to the restaurant where I joined a crowd of regulars. It might have been two days of hard effort on the bike, but I wolfed down the most delicious meal I’d had in a long time while a Red Sox game played out on the large TV behind the bar. It sure beat sleeping in a damp tent. The morning brought crisp blue skies and dry clothes, and I rolled out of the motel parking lot ready to tackle the remaining miles of trail ahead. It was quite a kick in the shorts then, when I started into the woods on the far side of Route 2 to continue my route. Immediately the trail was a minefield of deep mud and puddles filled to the brim with the fresh rainfall. My progress continued to suffer as I eked along through the deep sand of a series of sandpits that followed the mud. I didn't help that I struggled to find the trail. After some searching I found it slithering along the edge of Route 2 where it climbed abruptly on the rocky remains of an old road that was now something between a waterfall and a motocross trail.

At the top of the climb awaited the smooth doubletrack of the Ware River Rail Trail corridor. I headed south the doubletrack drew a straight line through backyards and an abandoned train depot. The further South I ventured the larger the river became on my left. This was prime trout fishing country, as the wide shallow river swiftly found its way through gentle rapids and wide eddies. The miles flew by as I rolled on a slight downhill all the way to Barre Falls Dam.

Turning east, I hooked up with singletrack near one of the flood control dikes of the dam and found myself on the best singletrack of the trip. Tight, smooth and fast, I rolled along a large swamp, eventually emerging into a sunny meadow where I set up my stove for lunch.

Dirt roads led me down to more singletrack and onto my arch-nemesis: the Mid State Trail. Thankfully, this was a tamer version of the monster that had beaten me up on a number of earlier encounters.

I wound through a pine forest and eventually through large open fields to the back side of Wachusett. From there, I jumped on the paved road around the mountain hitting a last bit of singletrack next to the reservoir, before zipping on pavement back to my start point: the Wachusett MBTA station.

As I rode the commuter rail back toward home, that cheesy Jason Aldean song about the two guys on an airplane dismissing the flyover states rolled through my mind.

"...Man it all looks the same,

Miles and miles of back roads and highways,

Connecting little towns with funny names,

Who'd want to live down there in the middle of nowhere..."

I guess until you've spent a night at Mud Pond, or rolled the fern lined singletrack in Ashburnham, or smelled the rain in Templeton State Forest you just wouldn't understand.

But, maybe its time that you did.

The Planned Route

My Packing List

Osprey Manta 28L Backpack

3L Reservoir

BRS-3000T Ultralight Camping Stove

Fuel Cannister




Wet Wipes

Large Ziplock Bags

Backup Battery


Feed Bag (Granola, Dehydrated Milk, Coffee, Sugar, Soup Mix, Cheese, Couscous,Taco Spice Mix)

Nalgene Bottle

Snowpeak Titanium 700ml Mug With Lid

Handkerchief (For grabbing hot mug)

Defiant Zipperless Frame Pack (Large)


Spare Tire

Chain Lube

Hand Pump

Co2 Cannister

Extra Stans Notubes Fluid

Rear Flashing Light

Revelate Designs Sweetroll Handlebar Bag (Medium)

Black Diamond Liquid Point Shell Jacket

Eddie Bauer Stormdown Hooded Jacket

Waterproof Pants

Eddie Bauer Synthesis Hoodie

Lafuma 30F Sleeping Bag

Wool Socks x 2

Wool Underwear x 2

Convertible Short/Pants

Long Sleeve Baselayer

Sea to Summit Ultralight Insulated Mat

Revelate Designs Mountain Feedbags (x2)

1 x Water Bottle filled with Electrolyte Mix

Snacks (Almonds, Gels, Waffles, Cliff Bars, Chocolate)

Revelate Designs Egress Pocket



Powerbank Battery

Watch Charger Cord

Phone Charger Cord

Bag Balm

Revelate Designs Pika Seat Bag

Hennessy Hammock – Asymmetrical Expedition Zip w/ Rainfly

Hennessy Hammock Snakeskins

1” Webbing x2

Rappel Rings x4

Carbiners x2

Although this is easily a two to three day ride, I recommend budgeting more time than usual, bringing along your fly fishing rod, and sampling some of the swift running rivers that line this route.

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