Thursday, October 14, 2021

2021 Pedaling Vacation in Greenport, NY

Despite initially feeling ambivalent about planning a 2021 vacation, once I made camping reservations, all the other steps fell in place, including my husband tagging along for a new experience.

That first day was an amazing adventure in itself, further heightened by the scenic Amtrak's Vermonter route and spacious seat (my husband would catch up a couple days later) within view of the vertical bike rack. My Rivendell Clem-entine exceeded Amtrak's stated maximum by 3", but it didn't pose any problems - I'm thankful employees hefted and removed my baby on both ends of the journey, 6 hours later rolling the bike onto the Hartford, CT platform. The only mishap occurred when I started rolling, stopping to inspect a rattling noise. The rear fender had pulled away from the bolt, scraping the wheel, but once I put it back, friction kept it in place. It held up for the entire 10 days, fortunately, because to re-secure it with a washer meant also removing the kickstand for Allen wrench access to the bolt head - a future project for sure!

Once on two wheels again, a heavy shower began and I ducked under an amazingly huge Gingko tree which acted as an umbrella for the ten minute deluge that eventually stopped, then navigated 20 miles of hilly terrain (thank you cue sheet), arrived at a prescribed spot (with my son's last minute texting help with route finding) at dusk where he then shuttled me and my loaded bike the last two miles (and 700 ft. elevation gain!) to his place. Phew.

On Sunday my son, his girlfriend, and her sister (who kindly put me up for two nights) went hiking on adjacent state forest trails - a spot where they also mountain bike. Later, we all went riding on the Farmington River Trail to Canton and back. Eventually two of us climbed the steep route back to their house - I made it unladen this time around - fortified with a drink and a brownie, initially to save an extra car shuttle, but it was also a worthwhile challenge. I'm glad I made the effort to visit our son on his home turf. He has lots of outdoor opportunities nearby!

My husband arrived on Monday then we drove to his brother's home close to Long Island Sound, leaving the car behind for the next week. Not only was this vacation about ocean views and beaches, but it was also a chance to visit family en route. As we set off to pedal the 10 miles to New London's ferry dock, we promised to spend more time  with his family upon returning. The direct route was hectic but the ferry ride was relaxing. After 1.5 hours, we disembarked at Orient Point where the 10 miles to Greenport was an easy ride, watching shore birds, the salty air reminding me how much I missed being near the ocean. Later, we set up our homes away from home (two small tents for comfort and organization - a first for us) for the next week at Greenport's municipal campground. When I initially planned the vacation, I imagined traveling by myself with freedom to possibly bike tour homeward - Amtrak one-way - but this thought also carried forward as a pair. With two full weeks off, being self-contained meant I had the liberty to follow through with solo adventures if I felt like it.

Lots of space to organize gear. I washed a couple items daily, letting them dry inside the tent on top of a yoga mat if rain threatened (I had hopes of continuing my daily yoga practice, but early darkness and getting plenty of daily exercise meant yoga practice fell by the wayside.)

My Cosmic Quilt set up - comfortable, loose fitting insulation on top, with a sleeping bag liner, cinched over a mummy-shaped air mattress, acted like a sheet. It's my new solution for more sleeping freedom.

After five years without an ocean fix, daily rides included hanging out at at least one beach, barefoot in the water, collecting shells. Late September weather was a perfect 60-75F day highs, with lows in the 50-65F range. 

Beaches varied. Some were pristine, sink your toes sandy; others were approached by stairs, with the beach composed of small ocean polished stones, often with boulders on guard like sentinels.

A heavy soaking rain storm was in the forecast, which arrived a day early. All indoor accommodation is expensive on Long Island so we opted for a night's stay in an RV - another first! Better than a motel for the same price, and self-contained - my husband's brilliant idea - so we quickly battened down
the tent hatches, pedaled quickly just before dark to a nearby private campground and enjoyed the luxury of the Treasure Ship, with our bikes safely stored beneath an awning. Afterwards, we were pleased that our tents and gear survived the downpour, with only minor puddles in the tent corners.

All bike touring vacations will have mechanical weirdness. After the initial fender problem, my front rack came loose, presumably from the ferry's vibration, but was easily fixed. On the other hand, my husband's rear tire developed a lump, which quickly grew worse. It was an older tire which needed replacement, so we discovered a bike shop a 15 mile ride west of Greenport. It ended up being fortuitous because we pedaled through the heart of the North Fork's vineyard region. Vines were heavy with grapes. After my husband swapped tires outside the shop, we returned to Greenport by a different, quieter route, looping behind the vineyards and vegetable farms, and eventually along the northern coast.

Greenport Harbor is also a fishing village...

So many unusual and wealthy vehicles used the ferries.
...And has frequent ferry service to Shelter Island. We spent a couple days pedaling around Shelter Island and took an additional ferry once to North Haven Island, continuing further by bridge to historic Sag Harbor. We visited the Whaling Museum, the only indoor touristy thing (for obviously reasons), but in the end it was a worthwhile visit. We also discovered a long distance walk/hiking access trail, which was fun for to ride for a short distance, though it's better suited to mountain bikes! 

I had high hopes to visit Montauk Point, but the distance/time from Greenport made it unfeasible as a day trip. The rainy forecast further upended the idea. Traveling with a companion has it pluses and minuses. I was thrilled to be with my husband, of course, but he is more frugal. Had I been alone, I would've sprung for a couple hotel nights closer to Montauk just to meet my goal. Also, we mostly shopped/cooked to save money. The last day I treated myself to take out fresh fish & chips plus we had a snack at an outdoor café - the extent of  restaurant-type meals. I also longed to visit a vineyard or two and enjoy the area's special vintages.

The boat in the foreground is normal size.
Greenport is a destination for yachts! There are large piers, open to the public, so it was an amazing sight to see them up close.

A lavender farm in East Marion.
We spent six nights in Greenport, leaving a day early because we'd run out of bicycle exploration ideas within a 30 mile radius.

Guard dog kept me company.
Parting Thoughts
Riding a bike to explore the Greenport region in the off season was an excellent mode of transport. We explored back roads and there was always room for us on the ferries. 

It's possible to camp to keep cost down with an occasional indoor splurge if necessary for comfort.

September, despite early nights, was a perfect time of year to avoid the tourist rush, especially mid week. Weekends were a bit busier and we shared the roadways with bicycle groups. Beaches were never crowded; often we were one of two couples enjoying the sand. 

Averaging 30 daily miles allowed enough time for exploration.

Other than a cartoony map provided at the campground to get around, information centers were closed or non-existent. We love printed maps, but needed to relay on phones for navigation. In the future, I would pre-print maps to have on hand because it seems counterintuitive to enjoy the outdoors and have digital devices as a necessity.

Next time I'll leave the yoga mat behind.

Since I loved the flattish terrain and coastal environment, I've investigated another Long Island adventure. With ferry service from the same New London port, it's possible to visit Block Island and end up in Montauk Point - a future adventure!

East Bay Bike Path.
On a side note, Connecticut is full of rail trails. We stayed with my husband's brother for two nights after navigating a safer and scenic route to his place. With a day to explore another region, we initially considered the Airline Trail, but it would require figuring out which segment was manageable for a day ride. Instead, we opted for an excursion on the Hall of Fame, East Bay Bike Path in Providence, Rhode Island. With it's bayside views, abundant marine wildlife, and wooded corridors, ending in coastal town of Bristol, it was an absolute pleasure!

We drove home the next day, planning to complete another scenic bike overnight during the rest of my time off, but weather thwarted plans. However, it happened the following weekend. Stay tuned for a future write up.


  1. A great trip Annie, a bike riding adventure. A wise move to keep the daily mileage reasonable which gives you the opportunity to explore and get the feel of the area rather than just pedaling through.

  2. Sounds like it was was a great get-away. Beautiful area.


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