In the Suburbs: Discovering the unexpected in Fairfield

Carin Jamieson and Ed Caliri of Newtown check out the books outside of the Fairfield University Bookstore at the annual Sidewalk Sale & Street Fair on Saturday, July 18, 2020, in Fairfield, Conn.

Carin Jamieson and Ed Caliri of Newtown check out the books outside of the Fairfield University Bookstore at the annual Sidewalk Sale & Street Fair on Saturday, July 18, 2020, in Fairfield, Conn.

Jarret Liotta / Jarret Liotta

Two weeks ago, as I was driving to work in Fairfield on Interstate 95 in the pouring rain, I glanced at a sign reading Accident: 5-mile backup. I was just approaching Exit 29, so I got off the highway and decided to make my way to Fairfield Avenue and get to my favorite diner in time for a quick breakfast.

Things were fine until I crossed Brewster Avenue in Black Rock. From that point, there was a wall of traffic, barely crawling toward the Fairfield traffic circle. The last broadcast I heard indicated that there had been a pre-dawn accident with an overturned tractor trailer and a vehicle and traffic would likely be blocked for hours.

When I finally pulled into the parking lot at the hotel next to the diner, it was already after 9:15 a.m. and as I woofed down my breakfast, I asked my favorite waitress Karen and my favorite hostess Danielle if they had any suggestions for short cuts into Fairfield.

I told them I was already planning to break the law by turning left out of their parking lot and risking a ticket. Karen quickly stopped me. “No, you don’t have to do that,” she said. “Haven’t you ever driven through the neighborhood where Ash Creek is? Just turn right at the next stoplight.”

“Can’t say that I have,” I told her. And we lived in Fairfield for 32 years. Where does this mystery road go?”

Karen said that the road wound around Ash Creek and ended up at one of the beach roads in Fairfield. She said not to worry and that I’d end up in the right spot.

So, I turned right from the hotel parking lot and right again at the first stoplight where Vinnie’s Restaurant is. I always thought the road was a dead end. Wrong! The sign I saw read Riverside Drive.

The homes along this winding road were diverse and lovely. I noticed that a few of the streets led to the marina off Old Post Road and many of those homes were gorgeous beach front properties. “How did I miss this?” I thought. For starting off the day under pressure, I was starting to feel very relaxed.

Where did Karen’s mystery road go? Actually, it ended at South Benson Road. After one right turn, I arrived at Old Post Road and turned left to finish my unexpected odyssey and arrive on time at the Fairfield University Bookstore.

While I certainly don’t advocate traffic diversions after auto accidents, my finding this mystery road through Karen was a really unexpected Fairfield discovery. And the drive was so relaxing, I’ve taken it after work on a few occasions. After a busy day at the bookstore, this short drive along Riverside Drive helps me decompress.

This past week, I thought about other mystery neighborhoods we’ve discovered in Fairfield. One of those was the Brooklawn Park area, which we moved to in 2001. Ironically, my wife and I kept exploring the area and taking walks there on Sundays. We saw so many beautiful homes in this country-club neighborhood and dreamed about one day affording the area. But we did and lived happily on Brooklawn Avenue and Algonquin Road for 14 years.

Close friends Andy and Carol from New Jersey reminded us of another special neighborhood just this week. More than 20 years ago, they lived in a lovely area just across and below Fairfield University in a lovely little Cape. We spent many wonderful times walking through their area and enjoying barbecues and holiday get togethers.

They were returning from the Cape and we grabbed lunch on Tuesday at Centro. Andy said, “I wonder what ever happened to our little Cape near the university. I think I’ll look it up on Zillow”

“Whoaa, take a look at this,” he said. Their tiny cape had been transformed to a multi-level, $1.2 million mansion. “And I lost money on the sale 20-some years ago.”

One last neighborhood discovery in Fairfield came when my wife and younger daughter were riding their bikes through the Crestwood section off Jennings Road and found a wonderful selection of stately older homes mixed with newer, equally striking newer homes. My wife returned home that day and said she’d found a perfect neighborhood.

An old friend, Debbie, lived there and many years later, we were invited to a party at hers and Michael’s home. It was gorgeous. Recently, I thought I saw a for sale sign. But that home was a real treasure, as was the neighborhood.

I think Fairfield’s many unusual neighborhoods (there are so many more that I haven’t mentioned) are the real calling card for our community. And you don’t need an accident detour to explore.

Steven Gaynes is a Fairfield writer, and his “In the Suburbs” appears occasionally on Fridays. He can be reached at