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Step 1
Decide which part of the trail you'd like to start at first. The western trail starts in Shelton and ends in New Hartford, and features 7 stops in the towns of Sandy Hook, Brookfield, Sherman, New Preston and Litchfield. The eastern trail starts in Wallingford and ends in Pomfret with stops in Guilford, Clinton, Stonington, North Stonington, Lisbon and Colchester.
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Step 2
Plan on spending one day each on the western and eastern trails. You could feasibly do both in one day, but it's recommended to take your time and enjoy each winery. To fully enjoy the offerings of each winery, plan on spending four days or so on the trip.
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Step 3
Pack a map, a picnic lunch, some walking shoes, a camera and a notebook so you can write down the names of the wines you like as you taste them.
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Step 4
Check the visiting hours of each winery to ensure that you'll be able to see them all within the time you have available (see Resources below).
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Step 5
Download a copy of the Connecticut Wine Trail brochure (see Resources below). This brochure offers detailed information about each winery as well as directions. It also contains a map and recommendations for nearby restaurants.
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Step 6
Call each vineyard or visit their websites ahead of time to find out about any special activities they have available for guests. Many vineyards offer carriage rides, horseback rides and special behind-the-scenes tours.
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Step 7
Give yourself some time each day to sprawl out on a picnic blanket with your picnic lunch (or take-out from a nearby restaurant) and a newly purchased bottle of wine. Most wineries will allow you to picnic in their vineyard. It's a great way to experience the beautiful sights and sounds of the area.
