YOLO: You only live once. Two years ago, September 25, 2018, I took a Tuesday off (random, right?) to fly to Chicago for the day. A combination of very cheap airfares and having never been to the Windy City was enough to entice me...
Last year I solo hiked Mount Washington, New Hampshire's highest peak, testing my endurance but paying me back with fabulous views and a feeling of accomplishment. The date? September 25.
And thus, a personal YOLO Day tradition began. Every year on this date I will challenge myself to do something interesting or unusual, often pushing the limits of how much one can accomplish in 24 hours. Always traveling. Always enjoying life.
So when 9/25/20 rolled around, I contemplated what I could do that would be safe amid COVID while still pushing the boundaries. The answer? Martha's Vineyard, the simultaneously rustic and swanky* island whose population swells from 15,000 to over 100,000 in the summer months. I had been once, 20ish years ago. My memories are vague, so I thought it was high time to return.
*By the way, the cute pink whale pictured above can be found everywhere on the island. Don't be fooled though, to get a piece of clothing adorned with his image will set you back - I calculated $358 for a full Vineyard Vines outfit!
September, I thought, would be the perfect time for a shoulder-season visit. I recruited my Dad for company, and at 5:50AM we were off and running.
PART I: THE FERRY
Arriving at the tidy, picturesque port of Woods Hole after two hours of driving and a 10-minute shuttle bus ride, we purchased our tickets and boarded the vessel. The 45-minute ferry ride was smooth and delightfully quiet, belied by the ferry's frumpy outward appearance.
We were treated to views of mainland Cape Cod on the left and glimpses of the Vineyard on the southern horizon. The water was buzzing with activity, quite literally, as boats ranging from pleasure craft to hard-working tugboats passed hither and thither. A Coast Guard chopper circled overhead, a roaring orange-and-white vulture.
The weather was perfect - sunny and surprisingly mild for 10am in late September. I enjoyed the warm breezes against my skin; my long sleeve shirt flapped carelessly as I peered across the water. The ship was empty enough that Dad and I literally got front row seats, eagerly anticipating our arrival in the Town of Oak Bluffs.
PART II: OAK BLUFFS
The town of Oak Bluffs somehow manages to be bustling and laid back. After disembarking the ferry we proceeded down the long wooden pier into town. Originally we were planning to take public transport around the island, but between COVID concerns and the added flexibility, we opted to spend some extra money on a car rental.
Passing by various souvenir shops and turning down a narrow lane filled with a relaxed, almost Caribbean vibe (perhaps it was the Jamaican flag in a restaurant window), we arrived at the car rental shack. In a scene reminiscent of a movie, we waited outside for 20 minutes as the customers ahead of us were invited into the minuscule building. The friendly employees (dressed in sandals and using laptops on a rustic wooden table) mitigated my slowly-gathering frustration at the delay. We hopped into our economy whip and made our way south down the island's east coast.
PART III: EDGARTOWN
Edgartown, sublimely situated at the island's southeast corner, is a portrait of quaintness and refinement. It's the island's Ivy League graduate older brother who now strolls casually about, adorned in $200 pink dress shirts, plaid shorts, and deck shoes. Let's just say Andy Bernard would fit right in.
After finally finding parking, we ambled back into town on narrow lanes surrounded by white picket fences, seeking a place to lunch. The weather had gone from mild to surprisingly hot, so I removed a layer and opted for flip flops. Near the harbor area where boats ranged from dinghies to million-dollar yachts, we happened upon a little seafood shack and decided to dine al fresco by the docks.
After lunch, we strolled along, popping into a few gift shops and avoiding the ones that would require a withdrawal from savings to make a purchase. The day was extremely pleasant, bucolic harbor views popping up between millionaires' simple yet sophisticated dwellings.
We made our way back to our woefully out-of-place economy car, as the clock was ticking on our day trip. After the slice of polished perfection that was Edgartown, we sought out the less populated side of the island, pointing the car west and traversing its rugged interior.
PART IV: UP-ISLAND
In island lingo, "Up-island" refers to the landmass's western side, far more rural and miles away from the hubbub of its three main eastern towns, Vineyard Haven, Oak Bluffs, and Edgartown. It took about 45 minutes to reach our destination of Aquinnah, and the somewhat peculiarly named Gay Head Cliffs. We found parking quite easily and scrambled up a slight incline for views that reminded me more of SoCal than anything I'd seen on the east coast before. The panorama was stunning, made all the more exquisite by the lack of crowds.
In addition to the cliffs, we took a trail that couldn't have been much more than 1/10 of a mile to the lighthouse, a brick beauty that had actually been moved back in 2015 to escape cliff erosion. A smattering of other tourists quietly moseyed; the 180+ degree outlook was simply stunning as I tapped away to capture it on my phone.
From Aquinnah, we proceeded east and then a bit north for a brief stop at the microscopic town of Menemsha, featured in a scene from JAWS. Ironically, we passed a man walking on the side of the road that looked suspiciously like Spielberg himself. His haircut probably cost more than my entire outfit. If Edgartown was the postcard-perfect GQ model, Menemsha was the scruffy cousin who shows up to family gatherings with unkempt hair and patched overalls.
Unpretentious wooden fishing shacks were sprinkled along the single dirt road, lobster traps and other tools of the trade haphazardly strewn around. Despite the area's rawness, it somehow managed to be equally picturesque, but in a grittier, more 'real world' sense. I could immediately see why Hollywood would want to film here.
The tiny harbor was quiet, but I imagined would turn into a hive of activity just before sunrise. A few vigilant gulls observed a scene that probably looked the same 200 years ago. I almost felt guilty snapping photos, imagining a Popeye-like character emerging from a faded shack to scold me with a brawny, weathered fist. As we turned around and proceeded back down the rutted dirt road I took a final shot of the bay, noting the name of a blue fishing vessel painted in simple white letters: Solitude.
PART V: OAK BLUFFS REDUX
Knowing we had to be back in Oak Bluffs for a 6:15 return ferry, we headed northeast from Menemsha, completing the roughly triangular circumnavigation of the island. Having seen E-town, OB was now looking rebellious by comparison - the cool younger sister with a piercing and some ink. Still refined, mind you, but with a bit of a wild side. We found parking by yet another classic harbor, noting that the air had already begun to cool by about 4:00. We quickly strolled through brightly-painted Victorian cottages and then sought out souvenirs for loved ones before an early dinner.
I was astounded at how crowded restaurants were at 4 in the afternoon. Upon passing a few rowdier-looking establishments, we settled in at Nancy's, a sprawling eatery with indoor and outdoor seating at the corner of the harbor. Given our timeframe, we reluctantly opted for an indoor table to avoid the wait, but were nonetheless rewarded with an enormous window on the nautical activity below.
Having finished our very tasty salmon sandwiches, it was finally time to return our vehicle and walk back toward the ferry. The sun was descending, but we were more than satisfied with how smoothly the day had gone, and how much of the island we'd experienced.
PART VI: THE RETURN
We were both exhausted, having been awake prior to 4am. We welcomed the opportunity to sit at the bow of another uncrowded ferry and enjoy a sunset, cool breezes, and gently lapping waves.
After a while the sunset became so stunning that the few folks on board began crowding one side of the vessel, attempting to capture it. The orb descended slowly, eliciting oohs and aahs before saying goodnight. The beauty was such that if the ferry ride had been the only thing I'd done, I would have called it a magnificent day.
For the third YOLO day in a row, I was reminded of the exquisite beauty of creation, the countless blessings in my life - including the friendship of my parents - and the unparalleled pleasures of travel.