Western Connecticut & The Lower Berkshires – Day 2

Connecticut is very nice

Diana and I spent Saturday August 30th doing a pre-ride of the scenic portion of our upcoming fall trip to Connecticut. As I mentioned in an earlier post I took a ride route from Moto-Maps and added The Southern Berkshires Loop that was listed in Motorcycle Journeys Through New England. The Berkshires are a range of low mountains in Connecticut, Massachusetts, Vermont and New York.

babbling creek in connecticut

Like most New England trips, the day started out rainy and cleared up in the afternoon. You have to have at least one of these days on every trip north. Between the weather and Diana’s hate for the killer pillow at the Motel it wasn’t the most enjoyable morning. I think having some traveling companions would have made this part of the trip more fun. We grabbed a muffin, juice and coffee at The Big Y grocery store which had a cafe. It was down the street from the Motel and very convenient. I never heard of Big Y before this trip.

cool old bridge

The beginning portion of our ride put us on Interstate 84 West for a little bit. This section of 84 was grooved and I wasn’t crazy about riding wet grooved Interstate first thing in the morning. Good thing I had a cup of coffee first. We got off the Interstate and our Moto-Map route of western Connecticut had us zig zagging northerly through classic New England backroads. The windy hilly roads are lined with houses so it’s not like you’re in the middle of no where like West Virginia; Diana kept calling it a residential road. Every so often we would pop into a tiny little town with a big white meeting house or steepled church in the center… then back into the pine tree covered hills. Up in Norfolk we cut west across Rt 44 and caught Rt 8 North. Rt 44 was one of our favorite roads we took coming across Connecticut from Rhode Island earlier this summer. Route 44 is a winner!

old new england meeting house

Coming up Colebrook River Road Route 8 through Winstead, CT is Colebrook River Lake and the West Branch Reservoir. About 3 miles before the Massachusetts state line is the entrance on the right to the Boat Ramp area maintained by the Army Corp of Engineers. Out of curiosity I had to check it out. It was a really neat area. There is a huge lake and hardly anyone around. There is a long beat up old road that runs along the water toward a dam. Having grown up on dirtbikes I couldn’t resist exploring the pot hole puddled cracked up old road to nowhere even though I was on a Harley. Good thing I got those new Progressive 412 series shocks. It was really cool; I felt like I was exploring way off the beaten path. You can check out the satellite view of this on Google Maps. The outhouse back at the boat ramp area made for a nice comfort stop. It was noon and we shed a few layers as the sun was starting to warm things up. We took a few pictures and got back on the road.

Boat Ramp Area

road to no where

gotta check it out

goofy Jay

princess of the boat ramp area

After that it was a short jaunt to the state line where we caught Route 20. Route 20 went through Lee and then we caught Route 183. Route 183 took us up into Lenox. I wish we explored Lenox a little more but we mistakenly rode right through in the blink of an eye. We stopped at the Norman Rockwell Museum on 183 but we didn’t want to pay $15 each admission and we were getting hungry. The museum is centrally located between Stockbridge, West Stockbridge and Housatonic. Diana found one of those cartoony maps that are very helpful in navigating small towns, this one is published by Miles of Smiles Directional Company. If you travel to the Berkshires call them at (413) 298-3999 to see if they will mail you a map.

Norman Rockwell Museum 

goofy jay 2

We were going to eat lunch at Jack’s Grill in Housatonic but it appeared to be closed. The whole town appeared to be closed. We continued on with our grumbling stomachs to the eclectic town of Great Barrington. I don’t know if there is a college nearby or what but we felt like everyone, especially young adults, swarmed into this little town. There were punkers, geeks and birkenstockers strolling Main Street. We checked out a coffee shop and a cafe before finding a sit down eatery that we thought was somewhat normal. We were wrong. The place was called Baba Louies and it was very artsy inside with curtains, candelabras, paintings on the walls and old music from the 20’s playing. I ordered us some Diet Cokes and the waitress told me they don’t have that. She was one of those wired frantic type waitresses freaking out because she had more than one customer and they were about to close for lunch. There was a carafe of water on the table so I poured us some water. It turns out the entire menu is organic foods and drink only. We ordered Smoked Turkey Panini sandwiches. You’ll be glad to know this sandwich is antibiotic and hormone free! I hate when someone slips antibiotics in my sandwich! I prefer traditional condiments or even organic condiments to Neosporin any day. No joking, these sandwiches were the tastiest sandwiches I ever had. They were bang’n! I recommend you try the Smoked Turkey Panini sandwich at Baba Louies if you stop into Great Barrington.

baba louies in great barrington

From Great Barrington we took Route 41 South back down into Connecticut. To quote Marty Berke, author of Motorcycle Journeys Through New England, “Route 41 is made for a bike”. To further quote Marty…

Route 41 meanders north past beautiful farms and through small villages with the Taconic Mountains providing a scenic backdrop to the west. Sharon, which was once an important crossroads, has immaculate Victorian homes lining the green, but each village strung along this route has its own charm.

In Sharon we got on Route 4 and then Route 7. We stopped at Kent Falls State Park on the left to check out the 200′ waterfall. It was a great picture op but we were attacked by swarms of pesty gnats that were intent on flying up Diana’s nose. This is a pretty stop and you should check it out despite the bugs.

Diana at Kent Falls State park

Soon after Kent Falls we merged with Route 202 and approached the New Milford area where we planned to meet up with my buddy John and his family. On Route 202 one of those new motorcycle commuter types who seemed to have recently dug out an old Japanese motorcycle from the 70’s or 80’s in order to beat the gas prices was riding in the lane next to me scratching his neck like he had fleas. Too busy scratching to wave at me or recognize a fellow rider. Of course I don’t think these guys get the brotherhood thing anyhow. Although he had a white full face helmet on, he was only wearing shorts and a t-shirt. Apparently he needed to run a quick errand to Home Depot because he started to take a quick turn and leaned the bike over to swoop into the parking lot. That’s when a huge pile of debris in the middle of the parking lot entrance caught my attention. I noticed it while passing by at 40mph from the corner of my eye, I don’t know how Mr. Scratchy Neck didn’t see it. Down he went! By time I was able to turn around and get back to him others had already stopped to help him up. He brushed himself off, rode the bike up to the lot and went into Home Depot with some minor scratches on his knee. I circled the Home Depot parking lot and got back on Route 202.

Jagermeister Truck

Just a few miles down the road we found the Octoberfest located across the street from New Milford High School. We couldn’t miss the Jagermeister Truck and big white tent. We met up with my buddy John and his wife who I haven’t seen in over 10 years. We had German beer and brats while listening to the oompa band. It was great catching up with my friends.

Octoberfest in New Milford, CT

After the Octoberfest we were invited to a little after party where we had beer, apple pie and of course… ice cream! Then we followed John and Margie to their home in Sandy Hook. They have a great house with a great guest room. We climbed up onto the guest bed which was about 4′ high and slept like logs.

the guest room

Use these resources to plan your own trip to New England (see below).

Moto-Maps is an excellent resource for scenic backroads and is available at www.Shop.RoadCaptainUSA.com

Motorcycle Journeys Through New England is also a great resource and is available through my Amazon store.

Click on the below pictures for more information.

Moto Map CT

Motorcycle Journeys Through New England