Traveling from New York, simply take exit 69 off of the Merritt Pkwy N. You will be on Route 66 in Meriden, and as long as you stay on that road, you will pass right into the north end of Middlefield. From Boston, Middlefield is less than 5 miles off of exit 20 on 91 S. From Providence, just take the route 66 exit off of 9 N, and follow 66 into Middlefield.
As Middlefield is as small geographically as it is in population, there are only two main state highways. Rt. 147 leads south into Durham and north toward Meriden. Rt. 157 heads west toward Wallingford and east toward Middletown. When navigating the town and its innumerable side roads, it is best to pick up a complimentary map from Town Hall, on Jackson Hill Road, just off of 157.
A great place to visit, with whomever you are traveling with, is Wadsworth Falls State Park. There are hiking paths, bike paths, picnic areas, open grass areas for sports, and a 30-foot waterfall. The park was dedicated to and surrounds the Wadsworth Estate, upon which sits Wadsworth Mansion. A quintessential New England Victorian, the mansion is worth a visit, and available for booking of formal tours.
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