When the National Trust for Historic Preservation went hunting for the nation’s “Most Romantic Main Streets,” Middletown topped the list. Here is what the Trust said:
“Middletown’s allure includes an artful Main Street brimming with elegant restaurants, an award-winning local chocolatier, and the romantic Inn at Middletown, offering the best of New England charm.
“Dream Date: With its views of Main Street’s church steeples and the winding Connecticut River, the Inn at Middletown is the perfect base for a romantic New England weekend. Make a leisurely start with brunch at the classic O’Rourke’s Diner, where the culinary talents of Brian O’Rourke have been celebrated by foodies from Gourmet magazine to The Food Network. Stroll along Main Street, and visit the vintage model train display at Amato’s Toy & Hobby, then stock up on regional treats at the New England Emporium. Malloves Jewelers just might give your sweetie some good ideas! Venture past the historic houses on tree-lined College Street to the prestigious Wesleyan University. Take in an eclectic and interesting lecture, a hockey game, or go stargazing at the college observatory.
“Back on Main Street, your hardest chore will be choosing where to eat. With dozens of choices in just a few blocks, you’ll be tempted by Mexican, Thai, Vietnamese, Japanese, and American restaurants, as well as the locavore, organic cuisine at It’s Only Natural. But for romance, try Esca’s extensive wine list and delicious Italian entrees—deemed ‘worth getting a babysitter’ for by local critics. After dinner, sample the artisanal confections at Tschudin Chocolates and a perfect espresso at Klekolo World Coffee. End your evening with a visit to Eli Cannon’s Tap Room for the best variety of local beers and friendly atmosphere, or retreat to the Inn at Middletown for a martini in front of the fireplace at the Tavern at the Armory.”