User Experience Design & Research
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Brooklyn to Boston by Bike (blog)

I spent five days biking from Brooklyn to Boston with my friends Matt and Jen in the spring of 2016. The weather didn't quite cooperate, but it ended up being an incredible and memorable journey nevertheless.

Shelter Island, NY – Newport, RI

Distance: 64 miles (102.8 km)
Elevation Gain: 2,704 feet (824.2 m)

There was a glimmer of hope this morning that we could avoid a hilly Connecticut/Rhode Island ride by going southeast to Montauk, taking a ferry to Block Island, and then another ferry to Newport, RI. But alas, the Montauk–Block Island Ferry doesn't run until Memorial Day, so no wimping out today.

Took off at 8:30 after breakfast pie and coffee, and Matt's meticulous route planning. The bell tolled just as we passed by the meeting house during a quick ride through Shelter Island to catch the ferry back to Greenport.

Still on ferry #1 at 9:10, and aiming to catch the 10:00 ferry to New London, CT, we booked it to Orient Point, covering the 9-mile ride, with 4 minutes to spare!

With 50 arduous miles ahead of us by the time the Cross Sound Ferry reached New London, we made use of ferry-rested legs, biking across the bridge to get to Groton. Enjoyed a scenic boardwalk ride and a paved trail through the woods, which brought us to a dead end, thanks to a draconian gated community. We were grateful the unpaved trail that took us around it was lovely.

By the time we reached Mystic, we decided it'd be smart to get to Westerly, RI—just over the CT border—for lunch. Westerly and Pawcatuck, CT share a business district; we had fun making frequent and necessary border crossings during our lunch break.

Fueled by the lobster roll, crab roll, conch salad, leafy green salad with chicken, and slice of pizza we shared for lunch, plus new air in our tires, we set out for the intimidating hills of Rhode Island.

Chase Hill Road was the first daunting one we hit. A resident driving up to his house beat us to the top, and congratulated us on our victory. He told us about the labyrinthine stone walls that run along the entire road—built by one man, as a sort of therapy.

Continuing on, we made surprisingly good time, considering today's total elevation gain was 2,076 ft, over 65 miles. Yesterday's 45 miles & 231-ft gain was practically a rest day!

We rewarded ourselves with fried clams—New England style, with bellies! Then we biked over to meet our Warmshowers.org host, Sondra. Warm Showers is pretty much Couchsurfing for the cycling community. Sondra offered to give us and our bikes a ride over the two Newport bridges where bikes aren't allowed, and a place to crash tonight. She and her partner Mary are amazing people. We spent this evening chatting about their cycling trips, canoe races, and all of Mary's marathons. She loves to run uphill at the youthful age of 84.

Katarina Yee
Port Jefferson Station – Shelter Island

Distance: 44 miles (70.8 km)
Elevation Gain: 844 feet (257.3 m)

There are some really nice people running the America's Best Value Inn in Port Jefferson Station. Last night's staff person was excited about our "expedition," and likened it to using martial arts to clear his mind.

We took off at 6:30 am to try to beat the rain rolling in. A tough start, fueled only by carob & spirulina energy chunks (BUT NO COFFEE), riding a mile or two on grooved pavement, followed by a decent sized hill. Thankfully, we spotted another sign for pie. Bought a delicious & huge rhubarb pie, day old for $9 (!) and finally some coffee, plus had some leftovers from last night—breakfast of champions! Legs felt a million times better after the meal (and coffee).

The drizzle that had begun just before our pie stop had become a bit steadier, as we entered the heart of the North Fork Wine Trail—25 miles of vineyards on either side, along with some bulls, cows, and ponies (though Jen says they were dwarf horses). The downside of biking is you can't miss any of the roadkill... today's most interesting was a fish!

Spent some time at the North Fork Brewing Company in Southold—so cute, nice people, and such good coffee! Boarded the Shelter Island ferry in Greenport by 2, saw some enormous and vocal wild turkeys, and stopped for a beer at the Shelter Island Craft Brewery before checking into our B&B just as the rain started to pour. A beautiful spot, and super affordable in the off-season—a perfect place to wait out the rain and rest after a 43-mile day.

Katarina Yee
Brooklyn – Port Jefferson Station

Distance: 70 miles (112 km)
Elevation Gain: 2,738 feet (834.5 m)

We hit the road at 9 am on this perfect weather day. The Brooklyn-Queens Greenway was a highlight, as was our stop for pie in Huntington at a 75-year-old farm. Stayed on Rt 25A for most of the way after our lunch stop, struggling up a few rolling hills, but nothing too bad. The Long Island Museum in Stony Brook has some cool outdoor sculptures and huge crocheted tree sweaters! Finally, we took a beautiful, but painfully hilly bike path during magic hour to Port Jefferson Station, where we're spending our first night. Had an insane amount of pasta for dinner at a great place called Renzo's. And dessert! Completely earned after a 70-mile Day One. Nervous about all of the rain in the forecast, so shooting to be in our saddles at 6 am tomorrow.

Katarina Yee