Two wheels, one island: A day of biking on Nantucket

Northeasterners never fight more fiercely than when they’re talking sports — except in the summertime, when they shift to arguments over which Massachusetts island is more idyllic.

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The rivalry between Martha’s Vineyard and Nantucket — the two major islands that lie just south of Cape Cod — isn’t quite as intense as the one between, say, Yankee and Red Sox fans, but it definitely exists. You’ll often catch a resident of one island insisting the other is inferior in every way. You’ll hear annual vacationers to one island tell you they’ve never visited the other and would prefer to keep it that way. In the local newspapers, you’ll sometimes spy writers making innocent jokes at the expense of their over-island brethren.

Countless thinkpieces and quizzes exist to help people decide which island is right for them, but I wanted to decide for myself. So in the midst of a long weekend on Martha’s Vineyard with my husband, I made the slightly controversial decision to, as the locals say, “get off the rock” and spend a day on MV’s easterly neighbor. (Our Airbnb host told us we were her first guests to ever venture to Nantucket during a stay with her, and she seemed a little disturbed by our decision.)

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For all their differences, Martha’s Vineyard and Nantucket have a major shared strength: great bike trails. Dedicated trails — that is, bike routes that are physically separated from car traffic — run up and down both islands, and because the terrain is so flat, it’s both possible and popular to travel between towns and villages by bike. Ian and I had brought our bikes along from Rhode Island and had already logged dozens of miles on Martha’s Vineyard. Now, it was time to check out Nantucket’s offerings.

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Though most of the island’s activity is concentrated in its one and only commerce center, which is simply called “Town,” I was dead set on kicking off our day here with an eight-mile ride to Siasconset. I’d been swooning over photos of the village’s signature rose trellises and classic red-and-white-striped Sankaty Head Light for years. Plus, I knew it was common to see seals bobbing in the waves on ‘Sconset’s beach, and I never pass up a potential seal sighting.

Our day began with an early breakfast on Martha’s Vineyard and an hour-long ferry ride from Oak Bluffs. There’s no denying that Nantucket makes a charming first impression from the water: Brant Point Lighthouse, wrapped in a giant American flag, protrudes from the harbor on a pristine spit of sand, and the surrounding shallows are dotted with colorful tall ships and fishing boats.

Tempting as it was, we didn’t stay in town long. After taking a few minutes to get our bearings and squeal at the adorable cobblestone streets, we began to travel away from the crowds. We stopped briefly to pick up some healthy snacks at Annye’s Whole Foods; then, we were headed due east toward ‘Sconset.

For most of the journey, our surroundings were sandy and scrubby, markedly different from the lusher and hillier terrain of Martha’s Vineyard. We let out amazed exclamations when, about halfway through the ride, we crested a gentle hill and were greeted with a sweeping view that bore a remarkable resemblance to the Serengeti. I had to remind myself that we were in New England, not Kenya, and a herd of gazelles would therefore not come bounding toward us at any minute.

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I know this photo doesn’t do it justice, but trust me — it looked otherworldly.

After a few more short miles, we journeyed from Serengeti to seaside village.

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“Village” is a generous term to bestow on ‘Sconset, which has little in the way of local businesses beyond a small grocery store, a sandwich shop and a clothing boutique. Yet on this particular day, the main intersection was jammed with cars, bikes and pedestrians milling around. It was a hot, humid day, and most of the crowds gathered under what little shade they could find, ice creams and ice waters in hand. Few of them were going where we were headed: to the sun-soaked Bluff Walk.

Once a fishing village with little more than a common well and a cluster of shingled shacks, ‘Sconset has evolved to become a community of mostly seasonal residents whose houses are considerably nicer than those fishermen’s huts of yore, though they’re still built with the same unpainted shingle siding. In July, though, that siding is slightly obscured…by mass quantities of roses.

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It seems that at some point, all the residents of ‘Sconset got together and decided to plant climbing roses everywhere. Almost every house has joined in on the fun, with many covering their shingles with giant trellises and coaxing the roses ever higher. On good years, they cover almost every surface of some houses.

One of the best ways to see ‘Sconset’s beautiful roses is by going on the Bluff Walk, a pedestrian path that begins not far from the village’s main intersection and continues north for about three quarters of a mile. The public path cuts through the ocean-view backyards of the 1 percent, which means your walk boasts not only sweeping views of the Atlantic Ocean but also a peek into the lives of some of the fortunate families who summer here. The path ends near the historic Sankaty Head Light.

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Unfortunately, two things prevented us from completing the whole Bluff Walk. One was the weather — we’d already spent about an hour biking in the hot sun, and we were too drenched with sweat to want to spend even more time fully exposed to the midday rays. Another was the slightly disappointing lack of roses. I’d been told that early July was the best time to see the blooms in all their glory, but it seemed they were blooming a bit late this year, as they were far less abundant than in the pictures I had seen.

No matter: When life hands you too much sun and not enough flowers, head to the beach and cool off in the ocean! We were thrilled to find a small public path that led us from the Bluff Walk directly to the sand below.

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Though we’d had bluebird skies on the bluff not 200 feet away, an eerie fog lingered right on the water. We were grateful to be shielded from the sun and promptly set up a little picnic with our supplies from the health-food store. Swimming, though, wasn’t in the cards: On this particular day, the waves were blood-red with kelp. We were unsure whether these were harmful algal blooms, but even if they had been safe, wading through them would have been uncomfortable and kind of creepy. Luckily, we stayed entertained from the shore as an adorable seal played hide-and-seek with us.

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After lunch, it was time to ride back to Town. For some reason — maybe it was the hot weather, or maybe the soreness from yesterday’s ride was beginning to take a toll —  the journey back felt much more difficult. Each little hill felt like an insurmountable mountain, and twice I begged Ian to stop and let us take a break. I was relieved when the trail leveled off and houses began to appear again.

We parked our bikes near the center of the action and spent a couple of hours wandering lazily down the Town’s cobblestone streets. The stately 18th-century brick houses lining Main Street, which reminded me strongly of Boston’s Charlestown neighborhood, seemed so out of place on a sandy island. I had to laugh, too, at the high-end urban clothing we spotted in some of the shops. What sort of person, I wondered, is in need of red-carpet formalwear, a full suit or a pair of equestrian boots while on vacation in the height of summer? Clearly I am not Nantucket’s target audience in many regards. But there were some things I did love about Town, including its abundance of adorable coffee shops and the fact that it has not one but two bookstores.

Nantucket was more crowded with visitors than anywhere we’d gone on Martha’s Vineyard — perhaps because there’s just one population center here — and after a while, we craved a little peace and quiet. It was about 3 p.m., too late to visit a cafe but too early to find many open restaurants. Finally, we found or, The Whale, a brand new restaurant with an attractive, shady patio, and posted up there with a glass of wine.

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Soon, it was time to catch the ferry back to Martha’s Vineyard. After browsing around some of the less preppy shops for a bit, we took our place in the ferry line, bikes in tow.

I came away from our day on Nantucket convinced that the island stereotypes I’d heard are mostly true: Nantucket is preppy, Martha’s Vineyard is bohemian; Nantucket is more corporate, the Vineyard is more artistic. As someone who grew up near a beachfront amusement park, I’m more partial to summer destinations that provide kitsch alongside class…so I’m probably more apt to stick to Martha’s Vineyard, where old-fashioned arcades and late-night donut counters exist alongside the million-dollar mansions and fine dining. That said, I’m dreaming of returning to this beautiful island in the fall or during the holidays. Is there anything better than a brisk, misty morning stroll down a cobblestoned street, especially a street that ends with this view?

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Sun, sand and sweat: Exploring Martha’s Vineyard by bike

I thought I was so clever.

I’d devised what I thought was the perfect affordable Fourth of July weekend with my husband on Martha’s Vineyard, the summer enclave that numerous presidents and celebrities call home. I had chosen to book a modest room in an out-of-the-way area to save money on lodging. I picked activities that were mostly free or cheap — beaches, parades, coffee shop lunches, happy hours. I had planned for us to park four miles away from the ferry terminal so we didn’t have to pay an exorbitant daily parking rate. And I chose a budget-friendly method of on-island transportation: cycling on our own bikes.

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On the morning of July 4, I was in smug self-congratulation mode as we pulled into our $0 parking spot, hopped on our bikes, strapped on our backpacks and pedaled toward the Martha’s Vineyard Fast Ferry in Quonset, Rhode Island.

And then I heard a loud POP! and a slow hisssssss.

We were, I kid you not, just feet away from the Fast Ferry’s ticket office when a giant rusty nail punctured my front tire. I let out a few choice expletives as my mind immediately navigated to worst-case scenarios. Was my bike totally out of commission for the weekend? Would I have to cough up untold sums of money for a replacement rental? It was a holiday weekend — would there be any rentals left? If not, how would we get around, and would bus tickets and cab fares end up emptying our wallets? Did one stupid nail just ruin our entire trip?!

Then, Ian brought me back down to Earth. There would be numerous bike rental companies near the Oak Bluffs ferry terminal, he assured me, and they’d have no trouble patching up the tire quickly. Everything would be fine.

He was right, of course. Once we’d docked, it took us all of 30 seconds to find Anderson’s Bike Rentals, where a very nice employee replaced my tube for just $20. Less than a half hour later, we were on the road toward our Airbnb in the town of Vineyard Haven.

The temperature was high and the sun was blazing. As we biked down East Chop Drive with several pounds of belongings on our backs, we began dripping sweat. Yet there was nowhere else I’d rather be. The sweeping ocean views, charming shingled houses and nautical decor around every corner reminded me why I’d fallen in love with the Vineyard on my first visit a year earlier, when I signed up to join a yoga and photography retreat hosted by my favorite travel blogger, Alex in Wanderland. The island has a way of easing troubles, slowing time and illuminating the truly important stuff in life — for example, the sine qua non that is tracking down the cutest lighthouse and snapping a million photos.

Our Airbnb was a modest but relaxing room in Vineyard Haven, one of the island’s six towns. Vineyard Haven, the main village within the town of Tisbury, doesn’t get much ink in travel guides. That’s partly because it’s less eye-catching than the other major population centers of Oak Bluffs and Edgartown, and partly because it’s a semi-dry community: There are no bars here, and the restaurants require you to order food with your beer or wine. But even if you like a tipple, I think there’s a case to be made for staying in Vineyard Haven. It’s more affordable, it has some of the best restaurants on the island, it’s just a short jaunt away from the nightlife in Oak Bluffs, and it boasts an artsy, bohemian community of year-round residents.

That said, we didn’t stay long in Vineyard Haven on this particular day. Once we’d dropped off our stuff, freshened up and met our lovely host Betsy, we were on the road again.

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First, we doubled back to the bustling, colorful, delightfully kitschy town of Oak Bluffs, where we dismounted our bikes and wandered around the Martha’s Vineyard Camp Meeting Association. The name probably conjures images of tents and cinderblock bathrooms, but in reality, the MVCMA is a neighborhood of ridiculously Instagrammable gingerbread houses originally built in the 19th century. Once part of a summer religious colony, the houses are now privately owned — I stayed in one of them during Alex’s retreat! — and today they are unaffiliated with any organized religion. But the historic Tabernacle at the center of the neighborhood remains and still hosts regular religious services, concerts and talks throughout the summer.

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Mid-afternoon was upon us, and the temperature was approaching 90 degrees Fahrenheit; needless to say, we were more than ready for a dip in the ocean. We grabbed our bikes and set off on the dedicated trail connecting Oak Bluffs and Edgartown, with plans to stop at a stretch of sand somewhere along the way.

This trail is unquestionably the flattest, shortest and most easily accessible one on Martha’s Vineyard, so we expected we’d be sharing the road with mobs of other cyclists on this holiday. To our surprise, the two-wheel traffic was pretty light, and we were flying by cars sitting in gridlock. It was just a few minutes before we found the perfect spot on Joseph Sylvia Beach.

After a heavenly hour or so in the water, where nary a shark was to be found, we were back on our bikes and headed toward Edgartown, home of the island’s annual Fourth of July parade. We were a little early for the parade, so we killed time by checking off another classic Martha’s Vineyard summer activity: a lobster roll picnic lunch at the local church. We paid $20 each for a gigantic lobster roll, a bag of chips, a bottle of water and the best people watching of my life, which for this island is a screaming deal.

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We weren’t feeling the parade vibes, so we skipped the beginning of the procession to check out the town’s elegant and remarkably uniform shingled houses and shops. My first visit to Edgartown had been in late September, well after the end of the typical island season, and most of the million-dollar waterfront mansions had stood largely empty. This time, it was different: Every house on Water Street was filled to the brim with celebrating families and decked out in patriotic streamers. Even the beach at Edgartown Harbor Light, one of my favorite lighthouses of all time, felt festive that evening.

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Still not ready for the noise and crowds of the parade, we opted instead for frozen cocktails on the patio of the Quarterdeck Restaurant. In the spirit of the Fourth, they were handing out free bottomless chips and salsa. With nearly everyone in town lining the parade route at that moment, the bar was blissfully quiet. A light ocean breeze cooled us off. My entire body relaxed. It was official: We were on island time.

After catching the tail end of the parade, we made the short bike ride over to Bad Martha Farmers Brewery and grabbed a sample flight. Just like the bike trail, Bad Martha was surprisingly quiet when I expected it to be choked with crowds. We spent a leisurely hour chatting and watching butterflies flit around the brewery garden as late afternoon gave way to dusk.

We hightailed it back to Vineyard Haven, then we grabbed our bike lights and pedaled toward West Chop in search of a good sunset overlook. The neighborhood was fairly rural and nearly pitch black; for about a mile, our bike lights illuminated a heavy concentration of mosquitoes and little else. Then we came across a country club where people milled around in pristine all-white ensembles. Though we felt out of place in our T-shirts and lycra shorts, we followed the crowd to an overlook, just in time for a breathtaking sunset. When we could stand the mosquito bites no longer, we headed back to our Airbnb and slept soundly.

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The next morning, we woke early to nab a seat at Vineyard Haven’s Art Cliff Diner, an island favorite. I was extremely tired and sore from the 25 not-entirely-flat miles we’d covered the day before, but pleasant thoughts of hot, strong coffee lured me onto my bike saddle and spurred me to start pedaling. We arrived just a few minutes after the cafe opened, and I was surprised to see very few people queued ahead of us. (I’m still getting used to the fact that New Englanders just don’t seem to be as gung-ho as West Coasters about early-morning breakfasts — a comparable cafe in Santa Cruz or Seattle would have been packed by 7 with a 45-minute wait list by 8, even in the dead of winter.)

An hour later, fully sated and caffeinated, we were off to a day trip on Nantucket — a post for another day! We returned at dusk and completed our tour of Martha’s Vineyard breweries with a casual dinner at Offshore Ale Co. After sunset, we dragged our sweaty, sunburned selves to Alex’s darling yellow gingerbread house to catch up over rosé. Somehow, I forgot to grab a selfie with her — but I did remember to document this unfortunate sunburn. Fail.

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The following morning, our last on the island, we both woke up with screaming muscles and foggy heads. Though we used to bike to work every day under the often-intense Colorado sun, we hadn’t spent this much time on two wheels in at least a year and a half, and I think we had both overestimated our physical limits. Though we weren’t quite ready to call it quits, we vowed to take it easier today, stopping when we needed and taking cover in the shade when possible.

This time we set our sights inland, following arterial roads and smoothly paved trails to the West Tisbury Farmer’s Market. We hopped from one outdoor stand to another, sipping coffee, munching on pastries, admiring island artists’ work and sampling locally-grown food. We loved bearing witness to the commingling of people from vastly different backgrounds here: We spotted preppy young families, bearded fishermen, gray-haired couples clad in tie dye, and of course former Secretary of State John Kerry.

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After we’d tired of squealing about the John Kerry sighting (me) and sipping the Single Greatest Lemonade Of All Time (Ian), we walked our bikes down the road for a little town sightseeing. West Tisbury is much smaller and more rural than the three easternmost towns on the island, yet its three-block-long main road is still bursting with art, food and entertainment. We first stopped at the Field Gallery & Sculpture Garden, where some colorful abstract paintings caught our eye. Then we pored over endless entertaining piles of bric-a-brac at Alley’s General Store, an island mainstay for many decades.

And just like that, it was time to pack up our stuff and go home. Before catching the ferry, we dragged our heavy backpacks into Mad Martha’s for a parting scoop of ice cream, then we briefly parked ourselves on a prime dog-spotting bench at Ocean Park to reminisce on the last few days.

We agreed that we had crammed too much activity, and too much bike mileage, into each day of this mini-vacation. Summertime in New England, in all its glorious brevity, tends to bring out the over-planner in me: I spend so many consecutive months in hibernation that, once the weather warms and the region explodes with events, activities and seasonal sights, I’m eager to do and see it all, to stock up on sunny memories that will propel me through the next hibernation period. But as I reflected on the long weekend, I realized that what endured in my memory weren’t the many pre-planned activities or the bike rides. They were the slow, spontaneous moments: our quiet happy hour in Edgartown, our afternoon swimming at the beach.

Was our long weekend celebratory and scenic? Yes, definitely. Was it relaxing and rejuvenating? No, not especially! Don’t get me wrong, I love being active while on vacation — but not so active that I wind up in a 24-hour stupor afterward. If we were to do it all over again — and I hope we do! — I would advocate for a week-long trip focused mostly on beachgoing, barbecuing, evening walks and one or two excursions to other towns. After all, in beautiful, seasonal, slow-moving places like Martha’s Vineyard, where the best moments involve sand, seafood and sunsets, the magic is in the dolce far niente — the sweetness of doing nothing.

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