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Overcoming doubt was just the beginning. Join Stephanie Kaplan as she tackles her first five-day tour from Vermont to Maine and discovers that fear and trepidation are always defeated by determination—and sometimes, cupcakes.

“What am I doing here?”

“Am I even enjoying myself?”

“Do I really want to do this?”

I try pushing these thoughts aside and start talking to myself.

“Left. Right. Left. Right.” I turn the pedals over, one laborious stroke at a time.

My face is dripping. The faint taste of salt hits my lips as I glance ahead, careful not to look for the top—don’t get fixated on the top.

Another question: “How did I get here?”

Adventure. It’s a BIG word that can mean a lot of things to a lot of people. To me, it’s diving into the unknown. Not knowing what’s ahead, what I might encounter, or even if I can complete the challenge.

That, in a nutshell, was how this trip was born. It came from the desire to test ourselves, our equipment, and our survival chops in a real world setting; riding around 350 miles in five days, from Montpelier, VT to Bar Harbor, ME. For me, there was also the added excitement of testing the new Dolce EVO on a multi-day tour. As part of the team who developed the bike, I was keen to get her out there and show the world what she could do.

My adventure partners on this trip included two members of Specialized’s “Seek and Enjoy” crew, Sarah and Erica; Beth Welliver, a badass rider and leader in the Adventure category at Specialized; and Bicycling Magazine’s, Cait Giddings, an adventure veteran with three cross-country trips under her belt. Then there was me: a bike "racer" and a complete newbie to bikepacking overnights.

We were practically strangers, which added to the "unknown," but no time to back out now. Time to get this show on the road.


The air was filled with anticipation as everyone readied their gear prior to roll out. Personally, I was a little terrified. Less than a year ago, this bike had been an idea in my head and now, here we were about to embark on a true test of its abilities. The doubt crept in. What if I’m too slow? What if I get dropped? What if something happens? What if we don’t get along? These thoughts were pointless, so I focused on calming my mind to concentrate on the task at hand—loading the bike.

Having short legs and a low saddle height meant I couldn’t fit a rear bag on my saddle, so I’d chosen to use a rear rack and Ortlieb Front Rider panniers. While I wasn't stoked on the weight distribution, I loved having ample room to pack and I ditched the idea of a front sack.

Packed and ready, we gorged ourselves on homemade French toast courtesy of Beth—one of the many skills she brought to the trip—and made our way outside to start our adventure. Our ride planning didn’t keep us in Vermont for long, but we were making sure we’d hit some of its culinary highs on our way, including my favorite: cheese. A short 25 miles later, pedaling some of Vermont’s smooth dirt roads, we arrived at the Cabot Creamery, which boasted a tasting room of over 30 cheeses. Perfect mid-ride food, right? After tasting pretty much one of every kind—seriously, the Everything Bagel Cheddar was a little slice of heaven. Run out and get it IMMEDIATELY—we loaded our back pockets with maple candies and continued on our way.

If there was any highlight from the day, it was when our route connected with the Cross Vermont Trail, a nearly 30-mile gravel trail across the state. The mostly hard-packed dirt and gravel was practically hero dirt thanks to rain the day prior, and suited our robust 32mm tires perfectly. Things were humming along smoothly when, part way down the trail, Caitlin ran over a branch and we suffered our first mechanical of the day. I removed the offending branch, which had lodged in her rear derailleur, but all of a sudden she’d lost the ability to shift and had to spend the next few miles riding her bike single-speed. Later, back on the main road and using some borrowed pliers and Beth’s “MacGyver” skills, we were able to reset the cable tension and adjust the barrel to get the bike shifting perfectly again.

While stopped for lunch, a sweet elderly lady approached to ask us what we were doing.

“Riding to Franconia Notch,” I said. She gave us a slightly worried look.

“Oh, good thing you aren’t going any further,” she said, “there’s a big rain coming. Big rain!”

My worry-brain kicked into overdrive. Big rain? What’s a big rain? I live on the West Coast—we NEVER ride in the rain (mostly because it never rains).

For the next 25 miles, to Franconia, I could still hear her words. I could still hear them as we celebrated the success of the first day, arriving at our inn at the north of town. I lay on my bed staring at the Weather app on my phone, contemplating in my head how we were going to get out of riding the next day. Maybe we could hitch a ride to the next stop? Or stay here while the storm passed? I looked over at Sarah and she sensed my worry—as all the girls did. She started to tell me stories about all the terrible weather she’d ridden in. Beth, with a degree in meteorology, looked at some of her "secret" weather sites.

“It won’t be that bad,” she said.

If they were calm, I could be calm, right? I fell asleep that night praying that the weather gods would spare our group.


Distance: 68 miles

Elevation gain: 4,621 ft.

View route on Strava


I got out of bed and looked outside, discovering my prayers had not been answered—it was pouring rain. I tried to stay calm, so as not to worry everyone, but my mind was imagining worst-case scenarios for us as we traversed New Hampshire along the Kancamangus Highway, or "the Kanc" as it’s more lovingly known. What if the roads were flooded? What if it was raining so hard cars couldn’t see us? What if we slid off the side of the road down a cliff? What if, what if, what if?

Sarah, my beacon for calm, was slowly getting herself ready and seemed un-phased by the conditions outside. Beth, Cait, and Erica, too. How was I the only one freaking out?!

A million excuses ran through my mind as I tried to figure out how to get out riding, but slowly, I accepted my fate. I’ll be honest: I was pretty motivated to get to the major food stop of the day in North Conway—a multi-time “Cupcake Wars” winner that we’d been alerted to by none-other than Lea Davison and her sister Sabe. When you want advice on where to eat and drink in Vermont, those gals know their stuff, and this one was a "can’t miss" #willrideforcupcakes stop.

Gearing up in my wool jersey—something I would realize later in our frigid descents that would be crucial—I slipped on a rain jacket to help keep the water out. Mustering all of my courage, I trudged down the steps like a child called down for school. Standing outside I was happy to discover that, although it was raining, it was at least warm.

We rolled out of Franconia for an easy 2.5-mile descent, where I was treated to the trip’s one (and ONLY) flat tire. Huddling under an apartment awning, I fumbled through my bags for a tube and pump and changed it quickly, and it wasn’t long before we were on our way towards the 13-mile climb to the top of the Kanc. Everyone told us that the Kancamangus was a beautiful road with heart-stopping views, but on this day, fog and rain completely obscured everything but the road ahead.

On a day like today, everyone had to ride their own pace to make it through, and after Sarah, Erica, and Beth quickly dropped me on the climb, Cait and I settled into the task ahead and chatted to pass the time. It’s amazing the conversations and connections that can happen while you’re riding a bike. We didn’t know each other, but by the end of the trip, we’d connected on so many levels and covered every topic; from our relationships to marriage and kids, to our favorite cupcake flavor (trust me, we were ALL riding for cupcakes that day).

12 miles later, we reached the top and found the girls waiting for us. The rain had given way to drizzle, and while my body was warm from the long climb, the faster girls were getting a little cold. We looked at each other, steeling ourselves for the 10-mile descent. And while the temperatures weren’t terrible, I was soaked to the bone and knew this would be challenging.

Clipping in, our rocket red shoes all in a row, we took off. Beth and Sarah, the most confident descenders of the group, disappeared into the fog and rain to fly down the mountain. I hung back, but as I got more confident, my speed picked up quickly. Just as quickly as the cold, the road got steeper, and I began counting down the miles to the bottom as I got colder and colder. Hands soaked and frozen, I began to shake violently, my eyeballs stung as the rain pelted my face relentlessly, and in the distance I saw a pair of rocket red shoes through the mist. I concentrated on those shoes, slowly reeling them in. When I caught up to Erica, we rode silently together, occasionally commiserating on how cold and wet we were while deciding what cupcake flavors we were going to get.

For the record, I was still focused on the Boston Cream.

Regrouping at the bottom, we rolled into North Conway and the White Mountain Cupcakery, a beacon of hope in an otherwise dreary day. Whoopie Pie, a Boston Cream cupcake, and a classic Red Velvet all found their way into my eager stomach. And after stuffing our faces with delectable treats, we begrudgingly hopped back on our wet steeds. Ahead lay the ultimate challenge of the day—Hurricane Mountain.

I’m just going to say it: Hurricane Mountain was, without a doubt, the hardest three-miles of riding I can ever recall doing. Bellies full of Boston Cream goodness, we hit Hurricane Mountain Road only a few miles outside town. It was a complete shock, and I was completely miserable. Weighed down by all of my traveling necessities, the road snaked upward relentlessly with switchbacks topping out at over a 20% grade. My face contorted in ways that I am ashamed to admit, and I’d be lying if I said tears weren’t mixed in with the rain. There were moments where I was certain that I would simply fall over, or that my legs would give out, or that I would lose that precious Boston Cream cupcake I had so coveted only 30 minutes prior. When we crested the climb in the pouring rain, and screamed down the other side—I’d never been so thankful for my disc brakes in the wet than then—I breathed a sigh of relief.

Shortly after, we completed our third state line crossing and reached our destination for the day, the Old Saco Inn. Maybe it was because we’d finished an exhausting and wet day, the warm shower, or the generous pours at the bar from Innkeepers, Peter and Sandy, but this was the most memorable lodging from our entire trip. We spent the evening in the main house folding laundry (thank you Sandy for doing three loads of dirty, wet, and stinky cycling kit), drinking some of the most amazing cocktails ever, trading travel stories, and eating great food.

I watched as Cait danced the Polka with another resident at the Old Saco Inn, and Beth perused Sandy and Pete’s photo album from their last Continental Divide motorcycle trip. I couldn’t help but think to myself, “There’s nowhere I’d rather be right now.” Honestly, I felt that way for most of the trip. It’s a rare time where you can really "check out" and focus solely on the ride, on present company and surroundings, and be "present." I think that’s something this trip taught me—never forget to be present.


Distance: 63 miles

Elevation gain: 4,666 ft.

View route on Strava


Truth time. I put a lot of energy into focusing on getting through the climbing, rain, and the wind of Day Two, so when I woke up for the third day of our adventure, I was overwhelmed by a deep feeling of exhaustion and dread. Looking around at my companions, I could sense that they were feeling the same way. Fortunately, that feeling was instantly washed away in the dining room when Pete and Sandy came out of the kitchen with homemade apple pie, stuffed French toast, fresh fruit, and copious amounts of coffee. It’s amazing how fast the sugar and coffee revived my spirits.

We retrieved our damp bikes from the garage and slowly loaded up for the day ahead, and I have to say that after two amazing—and painfully epic—days on backroads, today was a bit of a letdown. Our route took us on several main roads through Central Maine, and it ended up being a rather nostalgic day for me than anything of note. We passed a few miles from the summer camp I worked at during college, Kamp Kohut, and I yelled in delight as we passed the sign for it. To me, Maine seemed full of farm stands bursting with fresh produce, fruit, and pastries. MORE WHOOPIE PIES! By the end of the day, my legs were definitely starting to feel the rolling hills that New England is so famous for.

That night Erica had the genius idea to head to the local fireworks depot, and we spent the evening laughing and playing like kids with the sparklers. It was another one of those “I can’t imagine being anywhere but here” moments.


Distance: 78.4 miles

Elevation gain: 4,564 ft.

View route on Strava


My body was really starting to feel the effects of the last three days of riding—the most multi-day riding I’d ever done—but we were only one day away from our final destination, so I was feeling mentally energized. At this point, I had my morning routine down to a science. Get up, kit up, drink a lot of coffee, load the map on my Garmin, consult the printed map, and roll out. With Bucksport, our destination for the day, about 80 miles away, we had a long day ahead of us. Surprisingly, even with the distance, this ended up being our favorite day of the trip. This isn't because things went as planned (because they didn’t), and not because we got there easily (because that didn’t happen, either). We got lost and encountered obstacles in the form of a marauding army of bloodthirsty mosquitoes and waist-deep water crossings, and it was exactly BECAUSE of those things that it was the BEST. DAY. EVER.

The day started with us riding through a thick pine forest down a beautifully packed dirt road. And with the faint pine smell seeping into my nose, and the crush of the gravel under my tire, I was once again thankful to be exactly where I was with this group of amazing women in this moment.

I remembered that, during the initial route planning with Sarah, there’d been a day where we’d encounter some questionable "roads," but I couldn’t remember on which day. It became pretty apparent it was to be Day Four. By this stage, we knew each other pretty well and had an amazing attitude, and I think we all fed on the group energy to tackle each obstacle with reckless abandon and a carefree attitude.

With utter abandon in mind, we looked at the deteriorated road, thigh-deep water, and gigantic mosquitoes, and jumped right in. Hoisting our loaded steeds on our backs, we proceeded to wade through four deep crossings that day. You could hear yelps from Sarah and Beth up ahead every time a mosquito discovered one of their exposed limbs. Slapping, yipping, laughing, and maybe a few expletives found their way into the air, before we emerged on the other side, welt-covered and dripping. At this point, I looked around at the group to gauge everyone’s mood levels. Beth glanced over and let out a loud laugh and yelled:

“That. Was. Awesome.” And it was. Totally awesome—every wet and painful moment.

Hopping back on our bikes, we continued on our way towards a Maine staple: Young’s Lobster Pound. This widely touted "can’t miss" spot was still 20 miles from our destination, but that didn’t matter. Nothing would stop us. Every fiber of my being said, “Don’t eat clam chowder. Don’t eat a lobster roll, you’re going to get sick.” Those thoughts went out the window the minute we walked in and saw the food coming out of the kitchen. I went with the classic lobster roll and a cup of the clam chowder, and it was worth it. And while we were all nervous about eating such a heavy meal, we agreed that we would "take it easy" for the remaining miles so that we wouldn’t revisit some of the feelings we had on Hurricane Mountain days earlier.

In the end, we arrived into Bucksport easily. Sadness started to creep into my mind. Just like you get sad on Sunday morning knowing that the workday is just one day away, I was already thinking about the end of the trip. My thoughts floated away from the present and I began fretting about what lay ahead after the trip, plus all of the work I probably had to catch up on. STOP! Push those feelings aside. Concentrate on the now. This trip ain’t over yet!


Distance: 82 miles

Elevation gain: 5,026 ft.

View route on Strava


Getting up was HARD. I wasn’t used to so many hours on the bike, so my body was aching from head to toe. It was also hard because today was the "end." I think we all felt the finality of this. My emotions were a mix of excitement—we’d crest Cadillac Mountain and achieve everything we’d set out to do—but also sadness and dread. It would be over today and the real world was waiting back home.

We rolled out of the hotel with a quiet sadness hanging over the group. We had a lot of paved miles to cover along the heavily trafficked Highway 1 to get into Acadia, and my emotions were all over the place the whole way. I was annoyed at the paved route and the cars. I was annoyed that after today it was over. I was sad to leave the company of these amazing new friends. There wasn’t much chitchat from the group as we all dealt with the inevitable end of the trip. I wanted to make it to the top of Cadillac, and at the same time, I didn’t want it to end.

Acadia is known for its beautifully curated carriage roads, and it didn’t disappoint. We rode together to the visitor’s center, and as we looked at the map there, several people inquired about our group and where we’d come from. As someone who is new to this style of riding, I described with pride our 345- mile journey from Vermont to here. Looking at the map, I couldn’t believe that we’d really come this far, not by car, but by the power of our own legs. And all the stories we'd amassed each and every mile, each and every day. It made me feel so proud of our group.

Meandering our way through the park we followed signs to Cadillac Mountain. The night before, I’d started doing research on the climb, and I managed to scare myself (and everyone with me) about it. My legs were so depleted, but I was resolved to make it to the top. We took the left turn and had about four miles to reach the finish, and I decided to take it slow and absorb and enjoy as much of the moment as I could.

The road snaked gradually ahead, with multiple switchbacks, towards the top. Pine trees dotted the landscape, and the ocean sprawled out in the distance. It was a little overcast, but the views were breathtaking. I could see Beth, Erica, and Sarah up ahead, their red shoes glowing like a beacon as I slowly turned the pedals, inching towards the top.

With the girls cheering me on, I crested the hill into the parking lot and quickly put my sunglasses back on, fearing they’d see me crying. It was over.


We parked the bikes and walked along the rocky ledge, looking out on the horizon, back towards the direction we came. We’d ridden so far, seen so much, met so many people, and experienced so many amazing, scary, surprising and uplifting things. It sounds cliché to say, but this experience will stay with me forever. At the start, I’d been so scared of pretty much everything. Of myself and if I could do it; of my companions and if we’d get along; of what might go wrong along the way; basically, I was scared of the unknown. I considered many times not even starting this trip because of my fears and insecurities. Fear can be a powerful force that keeps us from trying new things and setting out on new experiences. It almost kept me from this one. Thankfully, I swallowed it enough to get on that plane and head to Boston, and thanks to these girls I was able to soak up their confidence and forge ahead, achieving something I didn’t think I could do. There aren’t words to describe how grateful I was in that moment.

I am hooked. This will not be the last time I tackle something like this, and truthfully this kind of riding consumes my every riding thought. I’m already planning the next one – where to next?! Need a wrap up to the bike.


Distance: 53 miles

Elevation gain: 3,625 ft.

View route on Strava


Written by Stephanie Kaplan

Photography by Christopher Lee, Matt Vandivort


Stephanie rode a Dolce Comp Evo with Roubaix Pro 32mm tires and running Specialized lights. She wore an S-Works Prevail helmet, RBX shorts and jersey, Grail gloves, Deflect Hybrid Jacket, and Motodiva shoes (in a special Rocket Red colorway).


Tuesday, October 6, 2015