Triple Plays

A good place to spend the night, interesting choices for meals, absorbing or entertaining things to do—these are the three basics we all seek when we travel. Here are some itineraries where the “threes” are wild.


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Middletown Rising

We may be biased, but we think downtown Middletown is the place to be. The city we affectionately refer to as “mini New Haven” has everything the bigger cities have to offer—culture, dining, shopping, luxury accommodations, a high-ranking university.

It even has a rich history. Main Street—where all the action is—is actually listed on the National Register of Historic Places. In Colonial times, Middletown was one of the country’s most important sailing ports and Main Street was its hub. Nineteenth-century industrial buildings still line the street, keeping the history and charm of the city alive.

There’s so much to discover here that it calls for an overnight visit or two. Book a room at the area’s finest hotel, the Inn at Middletown. Formerly a National Guard Armory, the historic hotel is nestled along the Connecticut River, three blocks from Wesleyan University and only steps from the shopping and dining district. The elegant rooms—100 deluxe rooms and suites, 12 executive two-room suites and one presidential suite—are decorated in charming country decor with Colonial-style mahogany furniture. There’s also a heated indoor pool and spa and fully equipped fitness center.

The hotel’s on-site restaurant, the award-winning Tavern at the Armory, takes you back in time with a menu of traditional regional and seasonal New England cuisine within the atmosphere of a charming Colonial tavern. Enjoy a bowl of New England clam chowder, the chef’s personal recipe for over 15 years, along with an imported lager and an entrée of surf and turf or Chesapeake Spice Pale Ale-batter-dipped fillet of salmon.

Another option is the Tuscany Grill, located in the beautiful Middlesex Opera House building. With live entertainment Thursday to Saturday, this fine Italian restaurant offers pasta dishes and pizza, delicious entrées—almond-encrusted salmon, Black Angus sirloin steak—desserts and an excellent wine selection.

Whatever you do, make time to drop by the famous O’Rourke’s Diner. A Main Street staple for decades, it was destroyed by a fire in August 2006 but, to the delight of many, reopened in February 2008 after the community held fundraisers to support the rebuilding process. Must-eats at this historic spot include a steamed cheesburger and a traditional breakfast of bacon and eggs.

After-dinner attractions are easy to come by in Middletown. Want to dance? Stop by Vinnie’s Jump & Jive, a community dance hall that offers lessons in everything from belly dancing and ballroom to swing and salsa. There’s also The Buttonwood Tree, a performing arts and cultural center. 

The main source of entertainment in the area is Wesleyan University. Its Center for the Arts is a performing arts complex—comprised of the Crowell Concert Hall, World Music Hall, Davison Art Center and the Ezra and Cecile Zilkha Gallery—that presents a wide variety of events and exhibitions, featuring everything from student and faculty works to internationally acclaimed ensembles.

For more information on the Inn at Middletown, call (860) 854-6300 or visit


Triple Plays

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