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Originally Posted by karenelizabeth
My boyfriend and I are planning a mini road trip up through New England this summer and are planning to make one of our overnight stops around the NY/CT border. Any suggestions for what town to stop in? We're in our mid-twenties and would probably prefer a smaller, more laid-back kind of town with some interesting restaurants/sites.
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In Northwestern Connecticut, there are many small New England towns with a laid back attitude and perfect for taking in the beauty of nature. Sherman, Kent, Washington Depot etc. all offer much in the way of scenery. There are vineyards, apple orchards, farm stands (seasonal), etc. The Litchfield Hills also offer hiking, skiing in the winter and Kent Falls is a perfect place to picnic. There are many celebrities, writers and artists who hide away in the hills because of the proximity to New York. So close, yet so far.
There are not many chain hotels in the area, but there are plenty of B&Bs.
INN at Kent Falls | An Historic Bed and Breakfast Located in Kent Connecticut. Enjoy Hiking, Antiquing, Skiing, Biking and more.
The Cornucopia At Oldfield Bed & Breakfast - Southbury, Connecticut -
The Heritage Inn - New Milford, Connecticut
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If you're more into being around lots of people and experiencing the local scene, there are many B&Bs in lower Fairfield County. This area is very affluent and lacks the laid back attitude that you seek, so you may be better off with the Litchfield Hills.
Connecticut Wine Trail - Wikipedia, the free encyclopedia
Look at the Western Trail because that is where you will be. The White Silo Winery is very nice. If you end up visiting Sherman, be sure to visit American Pie restaurant. Excellent American food with everything from wraps to burgers to eggs Benedict. You're likely to dine with locals rather than out of towners, which also makes it nice.
If you have anymore questions, feel free to ask and I will do my best to help.