Leaf Peeping Motorcycle Trip to Connecticut and Massachusetts

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Our First State HOG Fall Leaf Peeping Trip to Western Connecticut and the Southern Berkshires of Massachusetts was fantastic. Although I didn’t see the explosion of color I was expecting, the foliage was beautiful. Maybe you have to go to Vermont and New Hampshire to see the really bright colors. I hope Jokers Peeping trip to Vermont with Blackstone Chapter proved more colorfull. Foliage color is a complicated scientific phenom involving the types of trees, temperatures, timing, wind, rain and a bunch of other environmental ecological sociological wizardry. Our trees were a mixture of green, bright yellows, oranges, some reds and trees that had already shed their leaves. I may not know everything about leaves but I do know this… I love motorcycle trips with my HOG chapter! What could be better than riding with Diana and my friends through the twisty back roads of Connecticut and Massachusetts with the leaves falling like snowflakes and the orange and yellow colors of autumn surrounding us? I loved every minute of it! I can’t wait to do it again next year!

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We had 13 HOGs meet up at Mikes Famous Harley Davidson in New Castle, Delaware on Friday October 17th. A big grin spread across my face as I pulled into the parking lot to find my favorite wingman and tailgunner waiting for me. The three of us are a winning team, just like the New England Patriots! Steve and Kathie joined us and I really have to give them credit because the first trip I took them on was the infamous Soggy Bottom Ride to Mansfield, PA in freezing pouring rain. They were good sports about that Mansfield trip and came back for another! Gordy and Dolly had their Dyna Low Rider loaded in a new trailer behind their new Toyota 4Runner. My buddy Skip and his lady friend were there too. We also had a newer member with us named Ed who is very well traveled but this was his first trip with us. We hit the New Jersey Turnpike at 9:00am sharp with six Harley Davidson motorcycles and a Toyota SUV. Everyone had a CB radio except me and Skip. I think they were all talking about me the whole time. Of course I think everything is all about me. Am I wrong?

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We successfully navigated the web of roads that is Route 95 North entering Fort Lee, New Jersey. If you’re not careful you can end up in the express lane that forces you to cross the George Washington Bridge to New York. Miraculously we all got off in Fort Lee with no problems and gassed up at the Kwik Mart Luke Oil on Fletcher Ave Route 9W. Then we easily jumped onto the Palisades Parkway and stopped for lunch at The State Line Lookout 2 miles past exit 2. I love this place and their hamburgers. I wrote enough about State Line Lookout in two of my previous storys, so that I can’t do it again here. Our timing was perfect. We got there exactly at noon as scheduled.

Click here for my previous story about our trip with Skip to Rhode Island.

Click here for my previous story on the Labor Day Weekend Pre-Ride trip for this trip.

We crossed the Hudson at the Bear Mountain Bridge Route 6 East which leads you to the coolest cliffside twisty road. This is a must ride road. Then we ventured up Route 9 which was new to me. I tried to get us onto Dennytown Road in the Clarence Fahnestock State Park. Diana read someone’s post over at the Road Runner Forum that said this was the best road ever! I missed it and resorted to plan B which was bang a right onto Route 301. Route 301 is another must ride road! This is where all the rocket bikers in full leathers pretend they are at Laguna Seca. It is a killer road that follows the edge of several beautiful lakes and ponds and crosses one on a stone bridge. Riding Rt 301 on Friday and Sunday probably counts as the high light of the trip. Route 301 ends in Carmel, NY where we caught Route 52 to Route 6 east. Route 6 took us into Danbury.

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We visited the Harley Davidson dealership in Danbury. As Diana and I were checking out the t-shirts one of the attractive young sales ladies came over. She was a tall busty raven haired chick wearing a tightly fitted black top with a plunging neckline showing enough cleavage to knock Joker over… if you know what I mean! Anyhow it was what she said that knocked me over! She said “I have a rack over here…”. I didn’t hear anything she said after that but Diana tells me she had a rack of t-shirts that were on clearance. I was thinking “You sure do!”

We cut over to our Motel on Newtown Road in Bethel and unpacked. The cheapest Motel in the area is the Travel Inn of Bethel and with the exception of having pillows that are too thick it is a really nice place for the dough. The number is (203) 743-5990. If you call, ask for Vinny and tell him you want the Jay Green discount. We unloaded Gordy’s Dyna from the trailer and that’s when we found out it didn’t want to start. We got it going the good old fashioned run, push and pop the clutch way! We all took a dinner ride through the woods to the Sycamore Drive In Restaurant which one of our readers, Doorman, reccomended in a comment. The Sycamore Drive In Restaurant is an award winning 50’s style diner with a ton of memorablia. James Dean, Shirley and the Fonze decorate the walls as well as juke boxes, old fashioned cigarette machines, model cars and vintage gas pumps. It made for a great dinner stop! Thanks Doorman.

It was dark when we headed back to the Motel through the woods again. Country roads are great in the day, not so great at night! I missed a turn due to the darkness so we had to make an official FSH turnaround. We were almost back to civilization when I had to stop on a backwoods uphill road because a big ass buck was standing in the middle of the street chomping on a tree branch. He looked at me as if to say “WTF, I’m trying to eat here!”

Gordy is the life of the party!

Saturday morning we put on our cold weather gear, wiped the frost off of our seats and saddled up. It was chilly! Gordy decided to load his bike back in the trailer, leave the trailer at the Motel and follow by cage again. This might sound like a bad thing, but it worked quite well. It’s easy to see your sweep rider in a big silver SUV! I’m glad Gordy stayed and didn’t go home because he is the life of the party! Those who know him will all agree. Later in this story Gordy and I become blood brothers! We let things warm up while we breakfasted at the Blue Colony Diner on Church Hill Road in Newtown, CT. They treated us great at the diner. We ate big and then it was slightly warmer out for us southerners.

Moto Map CT

We zig zagged up through Western Connecticut following the Moto-Maps “Southbury to Danbury” purple loop. In Norfolk I caught Route 44 briefly which is a fantastic road that runs East/West across northern Connecticut. Then we followed the Southern Berkshires ride mapped out in Motorcycle Journeys Through New England by Marty Burke. We followed Route 41 South back down through the Berkshires of Massachusetts and into Connecticut. This is another must ride road! We took Route 4 to Route 7 to Kent Falls where we stopped at the picturesque Kent Falls State Park. We hiked up the waterfall trail a bit until we noticed it kept going up a lot higher than we were prepared to hike. Back down to the parking lot where it was getting darker out. We decided to head directly back to the Motel and eat across the street at a Bertucci’s and call it a night. We had a blast at the restaurant. The food (and beer) warmed us up after 8 hours of riding the chilly New England hills. Then we went back to the Motel for a good nights rest.

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The next morning we started to pack up the bikes when Skip discovered a problem with his Dyna Street Bob. I had brought a spare pair of motorcycle tie downs in case my Dyna Low Rider needed to be loaded on the trailer. Lucky for me, but not Skip, it was his bike we loaded onto the trailer with Gordy’s. While loading Skips motorcycle on the trailer Gordy cut his hand and was bleeding and didn’t notice it. I saw blood on my hand and thought I cut myself so I sucked the blood off my finger. That’s when Gordy and I became blood brothers! We will be eternally bonded! We said “Sayonara” to Danbury and hit the road again!

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I was the only Dyna left leading 4 Ultra Classics. Steve had an errand to run in New Brunswick, NJ so he pulled out of the pack once we hit the Turnpike on his two tone blue Ultra. Then I was leading 3 Ultra’s. Of course they were poking fun at my expense on the CB’s again; evereything is all about me. Or perhaps they weren’t talking about me. Maybe they were talking about Gordy passing us on the New Jersey Turnpike at break neck speed in his shiney new truck with the little trailer bouncing in tow with two Harleys strapped in it… probably one more than should have been in it. Off they went rushing to get back to Mikes Famous Harley Davidson in Delaware before closing to drop off the bikes for repair. Al pulled out of the pack on his white Ultra to follow the bouncing trailer leaving me with 2 Ultra’s.

When we got back to Mikes Famous Harley Davidson in New Castle, Delaware we were all reunited again and it felt so good! We grabbed sandwiches at Primo’s for dinner. Primo’s makes awesome subs. Then we hugged and said our goodbyes.  We have covered a lot of miles with some of our FSH brothers and sisters and it really feels like family when we travel together. It’s a little sad when we have to say goodbye knowing the trip is over (and it will be back to the grind on Monday morning). What am I talking about… it’s alot sad! Argh! To make things worse this is the last trip before the end of the season! Soon it will be too cold for me to ride and it will be time to winterize. On top of that I think this might be the last trip for Dianacam. Diana wants to ride her own on the next excursion. I might have to hire a photographer to ride pillion if we want to keep bringing you these great pics.

Diana and Jay at Kent Falls

Diana and I rode home to Newark, started a fire in the fireplace and drank hot cocoa. We thawed out in front of the fire from our blustery adventure in New England and went to bed with visions of red, yellow and orange leaves swirlling in our heads.

The End!

Special thanks to Mikes Famous Harley Davidson and Custom Cycle & Machine for having my motorcycle ready for this trip.