RC Ilumenati's Wings & Rings Ride SOMP

 Apr 21, 2025

We had a powerhouse crew assemble for this week’s Wings and Rings ride out of Fairfield. The roster included Scotty D, Abrehammer, Tadej, John K, Mat O, Johnny B, and yours truly, aka Snacks. Between a demanding workload and recent job stress, this was only my second time rolling out with the Ilumenati lately. As someone living the single life, I’m always eager to jump on any opportunity to eat out, grab some beers, and enjoy great company—it beats dining solo any day.

With the spring days getting longer, it was a welcome treat to kick off the ride while it was still light out. Starting in daylight is a huge safety bonus when navigating the busier streets of Fairfield and Westport before the evening rush completely takes over.

I planned a route designed to stay entirely South of the Merritt Parkway (SOMP). Heading into the interior of Fairfield, we made our way up old Morehouse Road and almost got T-Boned by a deer. 

If you haven't ridden it, it’s a beautifully bucolic, narrow lane that’s blocked to motor vehicle traffic on one end, making it a cyclist's haven. To top it off, there’s a charming little farm near the top where a few resident donkeys and pigs watched our paceline roll by.

Our navigation strategy down here is always about minimizing car interactions, so we stuck to the lesser-traveled backroads of Westport. Our classic routing eventually wound its way onto Imperial Avenue, which always delivers fantastic, sweeping views across the Saugatuck River. 

We crossed the river on the Saugatuck River Bridge which has an interesting history. The bridge, built in 1884, is the oldest surviving movable bridge in Connecticut and is listed on the National Register of Historic Places. Though, not the safest way to get across the river but the only way to get across the river to get to our next destination on this ride.

From there, we headed toward another local favorite: the Westport train station. We navigated the narrow catwalk running along the railroad tracks—an old commuter path that feels like it was custom-measured to be exactly as wide as a pair of bike handlebars.

The catwalk deposited us perfectly for a run toward Longshore and Compo Beach. Spinning through the grounds of Longshore is a great trick for racking up easy mileage while completely bypassing the busier main roads.

Exiting the park, we rolled past the iconic Minute Man Statue and coasted out to Compo Beach. 

A loop around the beach offers stunning views across Long Island Sound; on a perfectly crisp, clear day, you can even catch the New York City skyline on the horizon. 

The beach marks our traditional halfway point at about 15 miles—making it the ideal spot for a quick regroup and a nature break.

By the time we left Compo and climbed up toward Greens Farms Road, twilight had faded and it was officially time to fire up the helmet lights. 

Heading back into Fairfield, we buzzed past the Sea Grape and traced the spit of land out to the very end of Little Danbury.

We rounded out the night heading back toward the train station, taking a tactical detour through the alleyway right past Archie Moore's. We definitely caught a few patio patrons by surprise as a train of high-powered bike lights illuminated the alley, putting a perfect, lively exclamation point on a fantastic evening of SOMP riding.

At Archie Moore's, we ate our customary Buffalo Wings, Onion Rings, and well done French Fries and washed it all down with pitchers of PBR.