Connecticut shows its brightest colors traditionally in October; but this year September may be on point. The best places to visit are the wooded areas of the eastern Mystic region. All these places have delightful small towns and gorgeous scenic drives.
The Connecticut Wine Trail welcomes guests to wineries and vineyards that host harvest season events and tastings in fall 2022.
Essex to Guilford CT Shoreline loop drive -- 35 miles
This shoreline loop drive moves through the beautiful towns of Essex, Old Saybrook, Guilford, and Deep River, with stops at a marsh wildlife area and an ocean-side state park. 35 miles.
Nearby Points of Interest:
Essex Steam Train and Riverboat, One Railroad Avenue, Essex. Enjoy a lazy ride up the lower Connecticut River in the lavish, antique railroad cars, then shift to a Mississippi-style river boat to complete your journey on the water.
Hammonasset Beach State Park, 1288 Boston Post Road, Madison. Connecticut's largest shoreline park with lots of smooth beaches for swimming and sunning, along with a fun boardwalk.
Bishop's Orchards, 1355 Boston Post Road, Guilford. Fun place to get out of the car, stretch, and buy apples and pumpkins, and autumn treats. Great for kids and families.
Side Trips:
On the way from Essex to Old Saybrook, you can take a short side trip eastward on Route 95 across the Connecticut River to Old Lyme and visit the Florence Griswold Museum at 96 Lyme Street. This marvelous house operated in the early 1900s as a boarding house for a summer colony of New York artists, and it’s a hot spot for American Impressionism. You will see lots of art and beautiful gardens.
When you reach Hammonasset Beach State Park, swing northward on Route 450 for a stop in nearby Madison. There you will find a great bookstore, R.J. Julia Booksellers. Excellent book selection, gifts, kid's activities, and special events.
Dining:
Penny Lane Pub at 150 Main Street in Old Saybrook is an English-style pub and restaurant with a friendly, neighborhood atmosphere. Located on the state’s Signature Cocktail Trail.
Bufalina at 1070 Boston Post Road in Guilford serves authentic Neapolitan pizza from a wood-fired brick oven. Located on the state’s Pizza Trail.
Chamard Vineyards at 115 Cow Hill Road in Clinton has a very French-inspired bistro that serves lunch and dinner. Live music is presented on Friday through Saturday in the tasting room. Located on the state’s Wine Trail.
The Wharf Restaurant at Madison Beach Hotel at 94 West Wharf Road in Madison serves fresh and locally sourced foods that spotlight the flavors of the Atlantic Northeast and New England. Eat in the dining room or on the year-round porch.
Shoreline and Country Roads of Guilford, Durham, Madison CT -- 57 miles
This drive takes you from the Long Island Sound shore and inland among salt marshes, classic town greens, sunflowers and a fine farm stand. If you're coming from the New York/ New Haven area, take exit 53 off I-95 north. If you are coming from New York City, consider taking the Hutchinson River Parkway to the scenic Merritt Parkway (Route 15) as a substitute for I-95.
Side Trips:
About 4.5 miles east of Branford on Route 146, you might enjoy a small side trip to see the shoreline where ferries depart for the Thimble Island cruises. Simply take a right turn at Take It for Granite Antiquities at 409 Leetes Island Road (which crosses Route 146) and head south on Thimble Island Road toward the village of Stony Creek. After a breath of sea air or an island cruise, return to Route 146 via Thimble Island Road.
The Guilford green is a nice place to see a classic Connecticut town center. And the Guilford Art Center at 411 Church Street in Guilford may have something arty going on for your entertainment.
Durham is the northern terminus of the loop, and from here, the directions below take you back southward. For a short trip for pick-your-own apples, sunflowers, baked goods, and a great farm stand, head a little north out of Durham along routes 17 to 147 to Lyman Orchards at 32 Reeds Gap Road in Middlefield.
The shoreline is not the best place to see foliage, but if you love ocean beaches, you might want to swing over for a stop at Hammonnassett Beach State Park in Madison. Truly one of the state’s finest oceanside parks, with a walk and a nature center
