From Hartford and Points North -
- Route 91 South - Exit 22S (left exit)
- South on Rt. 9 to Middletown
- Exit 14, take left onto DeKoven Drive
- Turn Right onto Union Street
- Turn Right onto Main Street
From Boston -
- Mass Pike West to Rt. 84 (Exit 9).
- Follow Rt. 84 into Hartford and exit onto Rt. 91 South.
- Follow Rt. 91 South (instructions above).
From Southeast Massachusetts, Rhode Island, Southeast Connecticut -
- Rt. 95 S
- First right over Connecticut River is Route 9 N
- Rt. 9 N to first light (left exit) onto Rt. 66 W
- Turn Left onto Main Street. The Inn at Middletown is 4 lights up on the Left side of the street.
From New York -
- Rt. 95 N to 91 N
- Rt. 66 E at
- Junction Rt. 66 and Rt. 3
- Turn Right onto Main Street. The Inn at Middletown is 4 lights up on the left side of the street.
From West -
- Rt. 84 E to Rt. 691 to
- Rt. 66 E at
- Junction of Rt. 66 & Rt. 3
- Turn Right onto Main Street. The Inn at Middletown is 4 lights up on the Left side of the street.
From the Head of the Housatonic Regatta -
- From parking at Indian Well State Part
- Rt 110 South to Shelton center
- Left on Bridge Street to cross over to Rt. 34
- Rt. 34 South through New Haven to I-95/I-91 interchange
- I-91 North to Exit 18, continue to Rt. 66 East
- At Junction Rt. 66 and Rt. 3, turn Right onto Main Street.
- Turn Left at the 5th light onto Union Street.
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