One of my absolute favorite things to do when I am out riding around is to find roadside oddities and attractions. I have been known to make many a U-turn while driving down the road. This page will be dedicated to any roadside attractions that I have found in the state of Connecticut.
It will be a constant work in progress as I will add new oddities and attractions every time I find one. Make sure you check back often for new updates. Better yet, subscribe to my site so you will be informed each time content is added. Don’t worry, no spam here. I only send out emails once a week, usually on Fridays. Subscribe Here
Comstock Covered Bridge
Location: Comstock Bridge Road
City: East Hampton
Region of State Located: Central
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The Comstock Covered Bridge in East Hampton, Connecticut is a picture-perfect reminder of a time when bridges were built not just to be useful, but to last, and to look good doing it. Spanning the Salmon River, this classic wooden bridge was originally constructed in 1840 and is one of the oldest covered bridges in the state. Like many bridges of its era, it was “covered” to protect the wooden structure from rain and snow, which helped extend its life long before modern materials came along. Today, it still stands strong as a preserved historic landmark and a beloved piece of New England history.
While the bridge is no longer open to vehicle traffic, visitors are welcome to walk across it and take in its old-fashioned charm at a slower pace. The creaking boards, wooden beams, and filtered sunlight give the whole experience a nostalgic feel you just don’t get from concrete and steel. The surrounding river and wooded setting make it a great spot for photos, a short stroll, or a peaceful pause on a road trip. Whether you’re a history lover, a covered-bridge collector, or just someone who enjoys finding small treasures along the way, the Comstock Bridge is a simple but memorable stop that proves sometimes the best attractions are best enjoyed on foot.
Free Spirits Statue
Location: Mystic
City: Mystic
Region of State Located: South/East
Google Maps Pin
Located in Mystic River Park, this life-sized bronze sculpture depicts the legendary marathoner John J. Kelley running alongside his favorite dog, Brud. It is a beautiful tribute to a man who wasn’t just a local hero, but an international running icon.
- The Boston Connection: Kelley was a powerhouse in the running world, winning the Boston Marathon in 1957 and competing in two Olympic Games (1956 and 1960). He is often credited with helping spark the American running boom.
- A “Free Spirit”: The statue’s official name, Free Spirits, perfectly captures Kelley’s philosophy. He was known for his humble nature and his love for running in its purest form, often with his dogs by his side through the streets of Mystic and Groton.
- The Teacher and Coach: Beyond his own medals, “Johnny” was a beloved high school teacher and coach in the area for decades. He mentored generations of runners, including several who went on to become champions themselves.
- The sculptor: Brian Hanlon, captured the lean, rhythmic stride of a marathoner perfectly, making it look as though Kelley and Brud are about to run right off their pedestal and back onto the pavement.
Mystic River Bascule Bridge
Location: Mystic
City: Mystic
Region of State Located: South/East
Google Maps Pin
Located in the heart of downtown Mystic, Connecticut, the Mystic River Bascule Bridge is a rare and mesmerizing piece of maritime engineering. Completed in 1922, this historic “drawbridge” is one of the few remaining examples of a Bascule design, where massive concrete counterweights are exposed and move in plain sight to lift the roadway for passing ships.
- Engineering in Motion: Unlike many bridges that hide their machinery, the Mystic bridge features two enormous, 230-ton concrete counterweights that pivot downward as the leaves of the bridge rise. Watching the gears turn and the weights descend is a favorite “roadside show” for visitors.
- The Heart of the Village: The bridge is the literal and figurative center of Mystic. It connects the two sides of the historic whaling town, and its hourly openings (at 40 minutes past the hour during the season) dictate the slow, rhythmic pace of life in the village.
- A Photographer’s “Golden Hour” Spot: For your collection, the bridge is best captured at sunset or sunrise, when the steel trusses and the masts of the tall ships in the river are silhouetted against the sky. The nearby colorful storefronts and the legendary “Mystic Pizza” just a block away add to the quintessential New England charm. Unfortunately, I was there in the early afternoon…lol
- Historical Longevity: Having recently passed its 100th anniversary, the bridge remains a fully functional part of US Route 1. It has survived a century of salt air and heavy traffic, standing as a testament to early 20th-century American craftsmanship.
Stonington Point Light House
Location: 7 Water St
City: Stonington
Region of State Located: South/East
Google Maps Pin
The Stonington Harbor Light, also known as the Old Lighthouse Museum, is a small but historically rich landmark located at the tip of Stonington Point in Connecticut. Built in 1840, this lighthouse once helped guide ships through the busy waters of Long Island Sound and into Stonington Harbor. It remained in service until 1889, when advances in navigation and nearby lighting made it no longer necessary. Rather than fading into obscurity, the building was preserved and eventually transformed into a museum operated by the Stonington Historical Society.
Today, visitors can step inside the former lighthouse and explore exhibits that focus on local maritime history, fishing traditions, and life along the Connecticut coast. The compact space is packed with photos, artifacts, and stories that bring Stonington’s seafaring past to life. Outside, the surrounding park offers sweeping water views, ocean breezes, and plenty of spots to sit and relax. It’s an easy, enjoyable stop where you can learn something, take a few great photos, and appreciate how an old lighthouse found a second life as a keeper of local history.
The lighthouse is closed between the December 19th – May 6th. Use the link to the official Lighthouse website for up to date hours and costs.
Surplus Unlimited Cowboy
Location: 381 W. Main St
City: Norwich
Region of State Located: South/East
Google Maps Pin
Nicknamed Big Bob, the 22-foot-tall figure outside Surplus Unlimited is a classic example of a Muffler Man. These fiberglass giants were created in the 1960s by International Fiberglass and are a beloved staple of American roadside culture. Big Bob has become an official landmark for the city and a mascot for the store, appearing on their advertisements and delivery trucks.
Iconic Look: This specific model is a “Cowboy” variant, featuring the signature square jaw, a wide-brimmed hat, and a colorful vest and jeans that have been repainted several times to keep him looking sharp.
Patriotic Sentinel: For decades, Big Bob has been seen holding a large American flag. This “flagpole gambit” was a common tactic used by business owners across the country to bypass local height restrictions on commercial signage.
Amusement Park Roots: Before moving to his current location in the 1980s, the statue reportedly spent about 20 years at a local amusement park (and possibly a gas station) on the other side of town.
Durability and Defense: To protect him from high winds and occasional mischief, the business has secured him with steel cables. He has successfully stood his ground despite several attempts by locals over the years to topple him.
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