A Day Trip to Shelton

Connecticut has 169 towns, and it’s no secret that some get more attention than others. That’s only natural, and I’m a huge fan of some of the attention-grabbing towns (e.g., Essex.) I’m also excited (and just a bit apprehensive) to see some of my personal favorites become more famous in recent months (e.g., Stonington Borough.) Still, in my opinion some of the best local destinations are the lesser-celebrated ones. That’s partly because they haven’t become overly touristy yet, but it’s mostly because a lot of them simply happen to be fascinating places to visit.

Which brings me to Shelton.

Actually, what literally brought me to Shelton was a free half-day in the area and the memory that I really liked what I’d seen of Shelton in the past. I wanted to explore a bit more of this little city (which is not all that little by Connecticut standards, with an area of 31.9 square miles and a population of around 40,000.)

I start my day wandering along Howe Avenue, downtown Shelton’s main street, where small businesses occupy old-fashioned storefronts and historic factory buildings. Some of the shinier aspects of other Fairfield County towns have spilled over into Shelton due to geographical proximity, but the varied textures of its downtown are not yet close to being smoothed over.

From Howe Avenue you can walk across Bridge Street to Derby, a truly small city (Connecticut’s smallest, at just 5.4 square miles) with an unexpected number of sites to see. But today, it’s all about Shelton, so I stay on the west bank of the Housatonic River and stop at Three Bridges Coffeehouse (415 Howe Avenue), located in a rambling brick complex that once housed a hosiery mill, a corset factory, and a company that manufactured sponge rubber products. The coffee shop is quiet and cozy, decorated with exposed bulbs and star lanterns, and contains a cute little store, Willow & Ivy.

I drink my iced coffee and head towards the river, past the spot where the Shelton Farmers Market is held on Saturday mornings.

From there, it’s a quick walk to the water through the pleasant Riverview Park (799 Howe Avenue), a rectangle of open space featuring a war memorial, historic markers, and trails. I want to get a better look at a Shelton landmark, the 19th century railroad bridge that spans the Housatonic. I choose to view the bridge from the safety of the park, though more adventurous people do walk across it; it’s accessible a short distance down Canal Street.

Further down Canal Street, luxury apartment complexes coexist with historic brick buildings stamped with faded lettering and studded with star anchors. I could have spent hours on this stretch of road taking photos of these unintentional monuments to an erstwhile New England, a region that harnessed the powers of nature for industry.

Canal Street comes to an end at a foreboding-looking gate, but I don’t turn around. I keep walking to see the Shelton Canal and Locks, a site that feels like it must be off-limits despite the sign that says “All Welcome.” There’s a small display of historic photos and a brief explanation of the canal system and the locks, constructed in 1867, which allowed boats to reach the canal from the Housatonic. But aside from that, you have to use your imagination to picture canal boats rising in the narrow channel between stone steps and walkways turned feral by tufts of grass. This bit of industrial history has not been beautifully restored into a park-like environment like Lock 12 Historical Park in Chester, but if you like gritty, abandoned-looking places, that’s a definite plus.

The sun is shining down on the bricks and pavement and the day is getting hot, so I decide to explore some shadier attractions.

Leaving downtown, Shelton changes completely, becoming a blend of suburban-style residential and commercial zones and preserved natural areas. Trails, parks, and gardens, many of them centered around the Housatonic and other waterways, give Shelton the feel of a much more remote town.

To see some of its natural resources, I start small at Eklund Garden (10 Oak Valley Road). This secluded wildflower garden is built on a hill, and rows of stones give it a terraced effect. At first it looks overgrown, but when I walk further in, I see the order in this floral chaos and the carefully placed tags naming every flower. These are all plants native to the region (“plants that existed here prior to 1492,” according to the signboard that identifies them all.) From Eklund Garden, the Shelton Lakes Greenway Trail network extends in two directions. There are over 11 miles of trails in this system, and the bits I’ve glimpsed from the road look tempting. But I want to experience a more popular outdoor attraction in the city.

I drive down a stately stone-bordered road into Indian Well State Park (1 Indian Well Road), a long parcel of land stretched along the Housatonic. It’s uncrowded on this weekday afternoon, and peaceful with picnic tables and shade trees. The river changes quickly from brown at the bank to deep blue, and though most people here are swimming and fishing, I’m happy to gaze out at the houses on the opposite side.

In a separate area of the park is the waterfall that gives Indian Well its name. To reach it, I climb a dirt trail through a dark green wilderness beside a rocky stream. Hills covered with boulders and tangled trees rise above me. The waterfall, narrow and precipitous, is not the most spectacular in the state, but it is striking. Whatever you believe about the veracity of what Connecticut’s DEEP calls “the Romeo and Juliet-like Native American legend” of the falls, the spot does have an air of hidden drama.

The day is getting hotter still, so I drive a short distance to Wells Hollow Creamery (656 Bridgeport Avenue), a local favorite, for a frozen snack. Though just around the corner from busy roads and big box stores, this spot feels fully rural, complete with on-site cows and folksy touches like well-worn picnic tables and homemade signs.

And finally, because a balanced diet of iced coffee and frozen yogurt should always include wine too, I head over to meet up with the multi-talented Alonda (who took the photo of me in the About section of this blog) at Jones Winery (606 Walnut Tree Hill Road.) I think Connecticut’s wineries are some of the state’s best assets, and I haven’t been to this one before. We sit on the patio with our glasses of wine, surrounded by flowers and rustic farm buildings, admiring the winery’s pastoral and unpretentious setting. 

When I leave Shelton I have a renewed love of lesser-known Connecticut destinations – and a lengthy new Shelton to-see list for next time.


The easiest way to see the waterfall at Indian Well State Park is to avoid the main Park entrance and park in the lot on your right as you drive in, just before The Meadows. From there, walk across the street to the small trail entrance. This is a short and easy (though rocky in some places and occasionally slightly steep) walk up dirt path to the bottom of narrow falls. (A longer hike from another trailhead takes you to the top of the falls.)

Jones Winery is also a bustling pick-your-own farm (when I went, it was strawberry season) so be aware that the fruit-picking and the winery are actually different locations. Follow the directions on the winery’s website to make sure you end up in the correct parking lot. (You’ll see a cluster of red buildings.)

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