Although it is the third smallest state, Connecticut is one of the most beautiful by far. Heavily forested with miles of water access, the natural wonders abound throughout with history and culture around every bend. One of the easiest and best ways to see it all is to get behind the wheel for any one of the five most beautiful drives in the state.

Route 149, Colchester to East Haddam
Goodspeed Opera House
6 Main St.
East Haddam, CT 06423
(860) 615-4328

Distance: 12 miles one way
Price: $31 to $76
Hours: Wed – 2 p.m. and 7:30 p.m.; Thurs – 7:30 p.m.; Fri – 8 p.m.; Sat – 3 p.m. and 8 p.m.; Sun – 2 p.m. and 6:30 p.m.

Most of Route 149 runs parallel to the Salmon River and they both end up at the mighty Connecticut River. One of the most popular stops along this scenic, vineyard-filled road is the Priam Vineyards in Colchester. Guests there can get take a tour, sample locally produced wines and cheese, or pick up a bottle to take home, all while taking in a breathtaking view. The road offers some very pretty scenery along the way, but the best is definitely saved for last. Route 149 ends at the famous Goodspeed Opera House, more than a century old and still presenting theater goers with a spectacular experience. Those day trippers who are still looking to explore can continue on to Gillette’s Castle or head across the bridge to the quintessential Connecticut River Valley towns Haddam, Chester and Essex.

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Route 169, Lisbon to Woodstock
Prudence Crandall Museum
1 South Canterbury Rd.
Canterbury, CT 06331
(860) 546-7800
www.mystic.orgDistance: 32 miles
Price: $6 for adults/$5 for seniors or children
Hours: Available in May

Route 169 is one of only two roads in Connecticut classified as a national scenic byway (the other is the Merritt Parkway). Stretching 32 miles, this magnificent journey back in time offers travelers an idea of what the constitution state looked like when that nickname was first adopted. The omnipresent Connecticut fieldstone walls line fields throughout and help to frame impressive vistas. Travelers may also visit historical sites such as the Prudence Crandall Museum, shop for antiques or easily find the perfect picnic spot.

Related: Best Day Trips For Families Around Hartford

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Route 7 Kent to Route 41 Salisbury
Bull’s Bridge Inn
333 Kent Rd., Rte. 7
Kent, CT 06757

Distance: 33 miles one way
Price: $8 to $26
Hours: Mon to Thurs – 5 p.m. to 9 p.m.; Fri to Sat – 5 p.m. to 9 p.m.; Sun – 4 p.m. to 9 p.m.

This route follows a similar path to the Appalachian Trail from where it enters in New York near Bull’s Bridge to its exit into Massachusetts. The voyage begins in Kent, one of the best places in New England to view foliage. Continuing north, the road traverses Connecticut’s hill country, passing through or near more than 10 state and local parks, forests and natural areas. In Salisbury, a short detour on Route 112 leads to Route 41. This heads north through Salisbury’s delightful town center to the Massachusetts border. An extension of this trip to either border state is well worth it.

Route 94 Glastonbury to Route 85 Hebron to Route 16 East Hampton
Blackledge Falls
Route 85
Glastonbury, CT 06033

Distance: 20 miles
Price: free
Hours: dawn to dusk

Begin in the center of Glastonbury where Main Street meets Hebron Avenue (Route 94). Heading east, Route 94 goes over rolling hills past or near several working farms, Blackledge Falls and Gay City State Park. Continuing southeast, the road becomes Route 85 and goes through the picturesque towns of Hebron and Colchester. Route 85 takes a 90-degree turn at Broadway and runs past the charming Colchester Green. Veering off here to route 16 toward East Hampton leads to the Comstock Bridge, one of only three covered bridges in the state, making it more than worthy of a photographic pit stop.

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Route 146, Guilford to Branford

SBC Brewery
850 W Main St.
Branford, CT 06405
(203) 481-2739

Distance: 12 miles one way
Price: $5 to $20
Hours: Mon to Thurs – 11:30 a.m. to 10 p.m.; Fri to Sat – 11:30 a.m. to 11 p.m.; Sun – 11:30 a.m. to 9 p.m.

Connecticut is blessed with more than 300 miles of shoreline. One of the best ways to experience this is by exploring the coastal towns of Guilford and Branford. The narrow road meanders through several acres of salt marshes, which provide a terrific viewing experience for ornithological enthusiasts. Although the road offers excellent views of Long Island Sound, consider heading down to Stony Creek in Branford to rent a kayak or take a charter boat out to explore the Thimble Islands. End this day on the shoreline with a seafood dinner at one of myriad local establishments or a cool brew at SBC Brewery.

Related: How Would You Prefer To Spend The Day In Connecticut?

Charles Daniels grew up in Connecticut and after several years working and traveling around the country and world he has returned home for good. He lives in Hebron with his wife and daughter. While he wears many hats, he considers “part-time stay-at-home dad” his primary and favorite job title. His work can be found at