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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Celebrating love in verdant Vermont

In July 2018, on the eve of our second wedding anniversary, Ian told me he was whisking me away for a weekend. The destination, he said, was a surprise.

I was thrilled — I love a well planned surprise, especially when it involves exploring beautiful New England in my favorite season with my favorite person.

(That said — have you ever tried packing for a trip to an undisclosed location? I’m here to tell you it ain’t easy.)

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When we hit the road on Friday evening, I started narrowing down possible destinations in my head. I thought we might be headed to the Berkshires, which in the summer boasts not only natural beauty but also world-class culture: think classical music at Tanglewood and contemporary art at Mass MoCA. I also considered the possibility that we were on our way to the Hudson Valley, home of magnificent wineries, charming sleepy towns and an NYC-caliber restaurant scene.

But I was most convinced we were bound for Vermont, a state we both couldn’t wait to visit. On paper, Vermont seemed like exactly our kind of place: it had crunchy hippie roots, beautiful mountain scenery, a plethora of outdoor activity possibilities, and most importantly a lot of maple syrup and cheese.

As we crossed into the southeastern corner of Vermont — suspicion confirmed! — I was excited to see if the state would measure up to my Mt. Mansfield-high expectations.

Folks, it was love at first sight — literally. Within the first half hour, we hit this magnificent viewpoint:

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All at once, I realized why winter in Rhode Island felt so lackluster and why I missed Boulder so dang much: Because Rhode Island is as flat as a pancake! This was the first time I’d seen a mountain vista in six months. It was glorious.

As dusk descended, we pulled into the adorable town of Wilmington, where we’d be based for the next two days. “Town” is perhaps a generous descriptor of pint-sized Wilmington — it’s really not much more than a half-mile stretch of highway with a handful of restaurants, shops and adventure outfitters. Yet it has everything a discerning weekender could possibly want, including great food, an impressive roster of concerts and shows, and an amazing variety of handmade gifts to take home. Most importantly, it’s got that New England je-ne-sais-quoi about it — that woodsy, cozy quaintness I wasn’t sure existed beyond the pages of Yankee Magazine.

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After dropping our luggage inside the adorable Airbnb, Ian and I walked “across town” (read: two blocks away) for an uncharacteristically lavish dinner at Cask & Kiln, a relatively new restaurant housed in a historic brick building that had been ravaged by river flooding caused by Hurricane Irene in 2011. This place is as much about romantic atmosphere as it is about food, all low lights and leather tufted seats and Art Deco details. I loved that everything about the restaurant, including the decor, the menu and even the outfits of the servers, managed to feel at once contemporary and nostalgic, simultaneously casual and celebratory. The least classy thing about the place? Us — we had mostly packed outdoor adventure clothes and were easily the most underdressed people there!

The next morning, I woke up early to get the lay of the land. With a cup of coffee in one hand and a blanket around my shoulders, I read up on the area’s parks, attractions and seasonal events and consulted a map of the area. Soon I was fired up for a day of scenic hiking, kayaking, farmer’s markets and covered bridge peeping (it’s a real hobby!) — and I was already plotting return trips in the fall and winter, when the area appears equally gorgeous.

We kicked off Saturday morning with a Cajun-inspired breakfast at Jezebel’s Eatery and a brief tour through some of the town shops. Sometimes I feel like the same 50 books are on display in every bookstore, so I was pleasantly surprised by the eclectic and locally-focused displays at Bartleby’s Books. I think our visit here inspired about half of my holiday gifts in 2018!

After grabbing some local honey at a farmer’s market on the outskirts of town, we pulled into Molly Stark State Park — where we were stunned to discover we were one of just a handful of visitors that morning. After consulting a ranger and a trail map, we followed signs to the Mt. Olga Fire Tower, which promised sweeping views of the Green Mountains. Promise delivered.

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One thing I love about New England is its plethora of easy and moderate hikes. Many people who live in the West, particularly those in Colorado, approach hiking with a “no pain, no gain” philosophy and believe the best views can only be found by enduring grueling climbs. This 1.7-mile jaunt proves all those hiking snobs wrong.

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After Molly Stark, we reversed course, heading west on the state’s main southern highway with no particular destination in mind. Google Maps first led us to Woodford State Park, where we found a few-mile trail circumnavigating Adams Reservoir. Some families were paddling their kayaks and canoes on the calm waters, and we dreamed of returning here in the fall to do the same.

After relaxing for a while at the reservoir’s picnic area, we continued west and grabbed lunch at a bohemian coffee shop in Bennington. Wondering where to go next, we pored over the local tourism guides for inspiration. Almost immediately, we zeroed in on Bennington College — the alma mater of several big literary names, including Donna Tartt. We’d both recently read “The Secret History,” which was based on her time there, and we were intrigued to see if the place felt as mysterious as it had been portrayed in her novel.

The campus was beautiful, austere and almost disturbingly quiet in the middle of summer. We spent a pleasant couple of hours imagining spots where Tartt’s characters might have held their bacchanal or crossed the quad for Greek lessons.

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Back in Wilmington, we hit up Red Fox Shop, a local wine, cheese and gift store, to assemble our own ploughman’s dinner. The place was so unexpectedly delightful that we stayed almost an hour chatting with the owner, browsing funky cheeses and shopping for gifts. Then, we took our finds back to the Airbnb and lounged on the riverbank until the mosquitoes chased us inside.

On Sunday morning, we weren’t quite ready to return to the real world — so we took the scenic route home. Our first stop was a charming covered bridge near Brattleboro, the first one I’d ever seen on the East Coast.

After crossing into Massachusetts, Ian suddenly remembered one of his favorite area destinations from a previous trip here. Drawing largely from memory, he navigated us to the Montague Bookmill, a former 19th-century grist mill that is now home to a sprawling complex of used books, cafes, food stalls and local artists’ pop-up shops.

We had another three hours of driving ahead of us, otherwise I might have spent the entire day here. I loved everything about this spot — the sun-soaked reading nooks, the unpretentious vibe, the vibrant art, the friendly and talkative people.

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Needless to say, this weekend confirmed my assumptions that I’d love Vermont. Despite never having visited before, the Green Mountain State felt familiar to me. Maybe it’s because Vermonters seem so much like Santa Cruzans, filled to the brim with local pride and refreshingly far removed from the career-focused hustle of the I-95 corridor. Or maybe it’s that they spend so much more of their time outside, even in the depths of winter, like in our previous home of Boulder. Whatever it was, I know one thing: I’ll be back soon.

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READ NEXT: Two years in Rhode Island