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Middletown: Midwest Charm in Middlesex County

If you don’t have the time for a leisurely drive along the Mississippi, a trip to this city on the Connecticut will fulfill your need for old-fashioned wholesomeness and open space.

When I first saw the distinctive river towns of America’s heartland, I fell for them right away. They matched an image of this country I’d somehow absorbed, though I’d never seen anything quite like them in real life. I thought they were uniquely Midwestern, and that nothing of their kind existed in the Northeast.

Until one day I drove out of Portland, CT, on a sky-colored bridge, with two gently curved arches, a bridge that looked for all the world like something that should be spanning the Ohio. And then I continued into Middletown, and found a scene out of a story in Midwest Living. The spacious main street with its pleasingly mismatched buildings, the broad river curving alongside the town, the uncrowded parks and dignified houses on leafy streets. It even had a Route 66!

Middletown’s Main Street was named one of the nation’s most romantic by the National Trust last February. That might be debatable, but it is certainly one of the most visually striking.

It’s unusually wide, (wide enough for diagonal parking) and it’s also long, filling block after block with the diverse restaurants and shops typical of college towns.

One stop that would not feel out of place in Missouri or Illinois is Amato’s Toy and Hobby, a kid-centric chaos of playthings, model trains, and old-fashioned favorites (Silly Putty!) adults will love. Another, ironically, is the New England Emporium in the Main Street Market, part restaurant and part purveyor of regionally made goods like kitchen gadgets, beauty products, candy, and pet paraphernalia. All of which are so appealing and evocative of another time and place, you might forget what state you’re in once again.

A short drive from downtown is the Wadsworth Mansion at Long Hill, an elegant early 20th century summer house surrounded by woods. Built for Col. Clarence S. Wadsworth and his wife Katharine Fearing Hubbard, the property is now run by a charitable foundation. (The rest of the land became Wadsworth Falls State Park.) Wadsworth cared very much about the environment; now anyone can explore this lovely setting, designed by the Olmstead Brothers, and learn about its forests on two nature trails on the grounds.

Probably the most Midwestern place to eat in Middletown is Sweet Harmony Café and Bakery. The décor is replete with lace curtains and doilies, and you can eat your sandwiches, salads and desserts (their specialty is cake) while sitting in puffy armchairs in what might be someone’s Indiana living room. The service, friendly and relaxed, is also reminiscent of the Central Time Zone. And the knick-knacks are for sale.

Off of Main Street, side streets climb the banks of the Connecticut to the campus. Most of the houses in this area were built after the mid-1800s. Though Middletown began as a farming community in the 17th century , the preponderance of later homes, with their pretty lawns and shaded sidewalks, adds to the Middle American feel. The Wesleyan campus, as picturesque as a college on a TV show, is also a relatively late addition – it was founded in 1831.

And, of course, there’s the river. Like its counterparts in the interior, it was once a major thoroughfare. In the 19th century commercial steamboats paddled between Hartford and New York. Today you can watch the river flow by from the boardwalk or benches of . From here you can see the distinctive railroad swing bridge, and the pale blue Arrigoni Bridge, which initially drew me to this town and which still looks, each time I see it, like it might carry traffic not to Portland but to Kentucky or Tennessee.

If you go:

Wadsworth Mansion: The grounds are open from 8am to sunset. For more on the mansion, see the website.

Harbor Park: Open during daylight hours, entrance is free.

Sweet Harmony Café: Monday, 11am – 2pm; Tues – Sat, 11am – 3pm. For more information and menus, see their website.

Amato’s: Mon - Fri, 10am - 8pm; Sat, 9:30am - 5pm; Sun, call for hours. For more details see their website.

New England Emporium: Mon – Sat, 8am to 9pm; Sun, 9am to 8pm. For details see their website.

Parking in Middletown is plentiful but mostly metered. Some lots have machines that accept bills and credit cards, but for street parking, make sure you bring change.

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