The 7 Best Connecticut Road Trips

This beautiful state in Southern New England has stunning vistas from every point,, which makes Connecticut road trips some of the most spectacular in America. You can hop from small town to small town, while hugging the coast and absorbing the rich history along the way.

Connecticut driving routes are famous for fall foliage in October, with stops for picking apples, cider, or pumpkins. The summer months are also a delight, with beach stops the ideal way to get some fresh air.

The routes below vary in length; some are ideal for a day trip while others are more suited for a couple of days vacation with family or friends. Either way, you are in for a very special road trip…

The Best Connecticut Road Trips

1. Scenic Fairfield County

This route takes you through Fairfield County into the southern part of the Litchfield Hills region. Prepare to spend at least a full day or two exploring here: the city meets the country in this sophisticated region of Connecticut. From Greenwich to Stamford and New Canaan to Westport, you’ll find high-quality shops, classic antiques and sumptuous dining.

Distance: 115 miles

Route highlights: Maple Bank Farm; Woodbury.

When to do it: October for peak foliage season!

Image: @kevinjosephkeane/Instagram

2. New Milford, Kent, and Mount Tom State Park Loop

This drive is perfect for fall foliage! The route swings past the Housatonic River; near two covered bridges; through Kent and its many art galleries, historic homes and churches and then Mount Tom State Park. Stop off in the park to hike up to Mt. Tom Tower as well as enjoy swimming in the Mt. Tom Pond.

Distance: 46 miles.

Route highlights: Bull’s Bridge in Kent; Iron Mountain Preserve; Appalachian Trail.

When to do it: October.

Bulls Bridge | Visit CT

3. Route 136 – Darien to Westport

Also known as Tokeneke Road, Route 136 heads south from Exit 12 off I-95, eventually getting to the coastal section of Norwalk that’s known as Rowayton. It’s a village located within the city of Norwalk, that’s a picturesque New England coastal village surrounded on three sides by water. Stop off for fresh seafood along the route.

Distance: 8 miles

Route highlights: Rowayton.

When to do it: Summer.

4. Last Green Valley Scenic Byway

Drive through this lush, green region for classic Connecticut scenery. Throughout the region, you’ll also discover farmer’s markets, nature centers, vineyards, campgrounds, B&Bs, museums and all kinds of great places to stop, eat, play and stay.

Distance: 35 miles

Route highlights: Norwich; Brooklyn Green Historic District; Taylor Brook Winery.

When to do it: Year-round, but it’s best from late September – end of October.

Image: @river_rail_photo/Instagram

5. Essex to Guilford CT Shoreline Loop

This pretty shoreline loop route travels through the beautiful towns of Essex, Old Saybrook, Guilford, and Deep River, with stopping points at a marsh wildlife area and an ocean side state park. Be sure to swing by Bishop’s Orchards in the fall to pick-your-own apples and pumpkins.

Distance: 35 miles.

Route highlights: Hammonasset Beach State Park; Bishop’s Orchards.

When to do it: Year-round, but summer/fall is best.

Image: @mariapaz_gh/Instagram

6. Shoreline and Country Roads of Guilford, Durham, Madison CT

This beautiful drive takes you from the Long Island Sound shore and inland among salt marshes, classic town greens, sunflowers and a gourmet farm stand. There’s lots to see and do along the way, including a side trip on the ferry to Thimble Island or family fun at local orchards. See the route here.

Distance: 57 miles

Route highlights: Stony Creek; Guilford; Lyman Orchards.

When to do it: Year-round.

Connecticut Road Trips

7. Torrington to Norfolk Through People’s State Forest

Plan your road trip here to make the most of a full day spent exploring this picturesque forest. The park is home to he region’s finest fishing, hunting and winter sporting activities. Other activities include canoeing and kayaking, cross country skiing, field sports, freshwater fishing, hiking, picnicking, snowmobiling, and nearby camping at the American Legion State Forest.

Distance: 58 miles

Route highlights: Lake McDonough Park; Peoples State Forest & American Legion State Forest.

When to do it: Year-round.

Connecticut Road Trips

If you are spending time in the state check out The 7 Best Pizzas In Connecticut.

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Big 7 Travel Team
Big 7 Travel Team

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