The Glass House, New Canaan, Connecticut
Harf Zimmermann/The Glass House

For many road trippers, Connecticut is viewed as a big stretch of land on their way to other destinations in New England like Providence, Cape Cod, or Boston. Sure, there are cultural wonders to explore at Yale University, a couple of casinos to try your luck at, and vast areas of greenery — but is that all that the Constitution State has to offer?

During a weekend visit courtesy of the Connecticut Office of Tourism, we found far more to Connecticut than an Ivy League campus and slot machines. From wineries and kayaking to architectural feats and historic restaurants, the western part of the state makes an ideal road trip destination.


What to Do
Conveniently located right off I-95 in Westport is Downunder Kayaking, a one-stop shop rental for sit-on kayaks and paddleboards, along with a surf shop filled with equipment, sunglasses, swimwear, footwear, and more. Also on tap are one-hour group, private, or semi-private classes, led by one of Downunder’s knowledgeable experts. (We saw how diligent its staff is when our instructor, Seth, ever so graciously gave us a tug when we ran into some trouble.) Once it’s time to get down to business, you’ll be able to navigate three miles of flat water on the Saugatuck River, to take in sights leading up to the Long Island Sound.
Two-hour single kayak rentals are $44; doubles are $55. Classes are $55-$100.


Architecture and design buffs will love a trip to the Glass House in New Canaan. Built by architect Philip Johnson between 1949 and 1995, the Glass House is home to more than a dozen structures with a smattering of temporary and permanent exhibitions, including the namesake structure in which its designer lived for more than 50 years. The house has an open layout that provides panoramic, unobstructed views of wooded acreage, a bowl-shaped swimming pool, and guest quarters called the Brick House — look closely and you’ll see that it really does look like a giant brick. Step outside towards the back of the house for a glimpse of a pond that has a magnificent concrete pavilion sitting on the edge. Our favorite part of the tour was the inconspicuous painting gallery built inside a grassy hill.
Tours are $25 and run through November 30 this year.

Did you know Connecticut has a thriving wine scene? The Connecticut Wine Trail is made up of 24 vineyards sprinkled across the state. Our weekend itinerary took us to the family-owned Hopkins Vineyard in Warren, where we were treated to a tour of the facility, a tasting of seven different wines, and even karaoke by our fellow patrons. With the standard tasting, you’ll get to try six pre-set vinos, plus your choice of a medium-bodied dry red, peach wine, or a dessert wine.
Tastings are $7.50 and include a souvenir glass; bottles are $14.50-$41. Tours are $14 per person and require a minimum of 20 participants.

Where to Eat
With roots dating as far back as the early 1800s, Westport’s Tavern on Main is exactly what you’d envision when thinking about a quintessential New England tavern. It’s outfitted with plank wood floors, dark furnishings, and brick fireplaces, and there’s also an outside patio overlooking the shops on Main Street. Ambience aside, the restaurant serves lunch and dinner, plus weekend brunch. Tuck into Caesar salad with housemade croutons ($10) or challah French toast with seasonal berries and bacon ($13), or share a plate of smoked duck nachos served with fried dumpling chips, red onion, chipotle mayo, and lime crème ($14).

For a tribute to the country’s first president, grab a table at G.W. Tavern in Washington Depot. Named after George Washington in honor of his passing through the town, the restaurant is filled with depictions of the president through portraits, busts, and other pieces of art. New England comfort food is the specialty, with the beer battered fish and chips ($14) served in newspaper, along with a number of gluten-free options, too. And we highly suggest polishing off your meal with some sticky toffee pudding ($7).

Where to Stay
Lodging options in the area vary from chain hotels to full-scale resorts and bed-and-breakfasts. For those looking to stay at a boutique property, there’s the Ethan Allen Hotel. Decorated in neutral tones and outfitted with pieces from the Ethan Allen furniture collection, the hotel has 193 guestrooms — 131 of those are double suites that come with the luxury of a separate sitting area. While the furniture is likely to grab your attention, there’s an equally stunning outdoor gazebo that’s perfect for photo opps, too.
From $129 per night.

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