Isn’t the best part of autumn the sweater weather – those crisp, sunny days with the vibrant colors of the fall leaves changing from greens to reds, oranges, and yellows. And when you think of the fall foliage, classic New England comes to mind. Come experience autumn by taking a road trip through quaint, picturesque New England towns located in western Connecticut including:
- Gorgeous rolling hills of autumn leaves
- Farms, pumpkins, mums, apples, and vineyards
- Instagram famous shots
- Race car driving
- and…a Broadway star?
Welcome to my home turf, western Connecticut, a place rich in colonial American history and uninterrupted stretches of woodland beauty.
Connecticut is the third smallest American state by land area and is part of the New England region. It was one of the original 13 British colonies in American history. These colonies declared independence from the British Empire in 1776, leading to the formation of the United States of America.
The state has many influences from old England including names of towns and streets, such as Greenwich, New London, and Oxford, for example, and antique homes from the 1600 and 1700s built in the old English style.
Connecticut is located east of New York, south of Massachusetts and west of Rhode Island. Its entire southern border comprises of shoreline of the Long Island Sound.
On a fun side note, seals, dolphins, and humpback whales have begun to return to the Long Island Sound in Connecticut and just this year they tracked a great white shark in the Sound for the very first time!
Check out this whale watching adventure in Cape Cod New England here.
Take the scenic road trip of western Connecticut: Experience classic, rural New England on a gorgeous, autumn day. Go apple, pumpkin, and flower picking. Taste the local wine and apple cider. Smell the fresh air. See the farms and the rivers. It will be a great day in Connecticut.
First, check out this Fall Foliage map and Report to see how far along the leaves have changed colors in the Connecticut area.
The fall foliage season in Connecticut tends to start around mid to late-September. The season reaches its peak around Halloween to mid-November before the weather gets colder and grey nearing the Thanksgiving holiday.
Driving Route Through Connecticut
Here is a suggested driving route for road trippers that could be broken up into two parts. The entire loop is approximately 150 miles and can take anywhere between a half day to a full day to complete. This trip is a classic tour in America and a New England adventure.
Part 1, around the Litchfield area, comprises of a 120 mile loop.
Part 2, along the lower Housatonic Valley area, comprises of a 30 mile loop.
Depending from where you are coming, this scenic tour could begin and end at Interstate 84 in Southbury Connecticut or from Route 8 in Derby Connecticut that can be accessed from the scenic Merritt Parkway (Route 15) or Interstate 95.
Below is an interactive map of this route. Scroll down to the end of this post or click here to see complete driving directions in a pdf document ready for download.
Let’s get Started!
From Exit 15 on Interstate 84, take Route 6 North towards Woodbury. Drive through historic Southbury into Woodbury.
First settled in the late 1600s into the 1700s and 1800s, this area shows its rich history from the time of the British colonies to the Revolutionary War to the formative times of the United States of America and beyond.
A Broadway Star
For all of you fans of the Tony award-winning Broadway show Hamilton, the code word is “Rochambeau.” The Hamilton performance of “Yorktown” is about the battle of Yorktown in 1781 during the Revolutionary War, and Rochambeau is mentioned in the song.
A French nobleman and general by the name of Jean-Baptiste Count de Rochambeau played an important role in the American Revolution. He and his troops marched through this area of Southbury from Rhode Island on their way to Yorktown, Virginia. Rochambeau joined the patriots of the American Continental Army in their fight for independence against the British. Southbury’s middle school is named after Rochambeau.
Drive along Route 6 into colonial Woodbury, Connecticut’s antique capital. See the chickens at the plant nursery and stop for a quick ice cream next door. Here, a bold chicken is looking for Joanne to give it her ice cream cone.
And for you Gilmore Girls fans, Woodbury is mentioned often on the show.
Experience an example of a classic New England vacation in a little section of history along Old Route 6 – Veteran’s Way. Park the car and go for a short walk along the sidewalk to see the old homes, churches, and antique stores.
From here, take a left at the stoplight, just after the white steeple church, to Route 317 West. Beyond this stoplight on Route 6 is the LaBonne’s grocery store. Talk about a small town, small world – We met the owner of LaBonne’s at the gate to our flight to Dubai in the JFK airport in New York City. He was on his way to Asia while we were on our way to the Middle East. Click here to read and hear the podcasts about our Middle East adventure to Jordan and the United Arab Emirates.
Farms, pumpkins, mums, apples, and vineyards
Route 317 West will take you through the charming, rural town of Roxbury, home to a few famous artists, actors, and others looking for some peace and quiet in the country. The revolutionary, Ethan Allen was known to have lived in Roxbury. Notably, Roxbury had an important granite mine called Mine Hill that provided granite to build the Brooklyn Bridge and Grand Central Terminal, iconic places in New York City.
Pass along the white picket fences, farms, cornfields, and an airport, Good Hill Farm Airport, located on a large field of grass.
Heading through this quaint town, you will see a few white churches, characteristic of New England.
Stop off at the Maple Bank Farm on the left side of the road to pick up some pumpkins, apple cider, gourds, and farm grown vegetables.
At the intersection with 317 West and Route 67 North, take the right on Route 67 and pass the old gasoline sign. Drive along this woodland way and enjoy the backwoods.
Take another right at Route 199 North towards Washington Depot to the end of this route. Washington Depot was the inspiration town of the TV show, Gilmore Girls. Here, make a left onto Route 47 North, and pass through the campus of the Gunnery, one of the many iconic New England boarding schools.
The colonial town of Washington is located at the southern foothills of the beautiful Berkshire Mountains, named by the Nature Conservancy as one of the 200 Last Great Places.
Take a quick side trip to Averill Farm, pumpkin patch, and apple orchard, located just two miles from town. Pick apples and pumpkins at the farm, and while you are there, try their cinnamon donuts and apple cider.
After making this idyllic stop at the farm, backtrack to Route 47 North. Take a left onto Route 202 West and then quick right onto Route 45 North for a scenic drive along Lake Waramaug through the rural town of Warren. Turn left onto Route 341 West, and drive towards the town of Kent. Turn right onto Route 7 North, and make a quick stop at this quaint New England town. Pop into the little shops and cafes, and take in the fresh air.
Located along Route 7 North is the well-known Kent Falls State Park that has its classic, red covered bridge and a small waterfall located at the end of a short hike. Enjoy the fall leaf colors.
Continue onward on Route 7 North for a scenic New England drive along Housatonic River and through the Housatonic State Park.
Race Car Driving
Looking for a thrill? Check out the Lime Rock Speed Raceway located at 60 White Hollow Road in Lakeville located off Route 7 North. With some advance planning, you could even spend half a day learning how to drive a race car around their high performance race track.
Devin and Joanne went for a spin on the track after getting an introductory lesson on how to drive race cars. As they zipped around the track, I enjoyed the experience from the pace car.
Gorgeous rolling hills of autumn leaves
After completing a few loops around the track, head back down Route 7 South to see another classic New England covered bridge off Route 128 East. This bridge spans the Housatonic River connecting West Cornwall and Sharon Connecticut. Check out the Wandering Moose Cafe on the other side of the bridge.
Head back over the bridge to Route 7 South along the scenic Housatonic River. Turn left onto Route 4 East (Bunker Hill Road). Look out your window: The landscape opens up to rolling hills in the distance. On the way, pick some flowers at Something To Crow About dahlias farm located on the left at 34 Bunker Hill Road.
Route 4 East will bring you towards Goshen, Connecticut, a rural farm town. At the four way intersection with the flagpole in the center and a classic white church ahead, take a right onto Route 63 South. Explore the countryside, passing the Goshen fairgrounds on the left, and vineyards, and cornfields.
Route 63 South will bring you into the historic town of Litchfield, past the many historic homes of the 1700s colonial New England.
Nestled far into upstate Connecticut, Litchfield was an epicenter of the intellectual golden age in New England around the late 1700s into the early 1800s. Many leading government figures of the day came to study law in Litchfield, where the first law school in the United States, Litchfield Law School was located.
In addition, American abolitionist and Uncle Tom’s Cabin author Harriet Beecher Stowe was from Litchfield.
At the four-way intersection is the old-fashioned downtown. Park your car here and explore the stores, restaurants, and small park.
But save some of your time to pay a quick stop to a local vineyard and winery, just one mile from town, to sample some wines. Haight-Brown Vineyards is located at 29 Chestnut Hill Road. At four-way intersection, head to Route 118 South for 1 mile and take a right onto Chestnut Hill Road.
Continue on the tour, head towards Morris Connecticut. Backtrack to the little downtown and take Route 63 South where you will see more beautiful, historic homes. Take a right onto Route 61 South and then a right onto Route 109 West.
Visit Amanda Bakes in her vintage bakery trailer, parked most times at the Morris Marketplace, and pick up a freshly baked chocolate chip cookie.
This Part 1 tour is about three quarters of the way through. From Morris, turn left onto Route 202 West and drive towards the old-fashioned New England town of New Milford.
Among many movies filmed here, the Adam Sandler movie Mr Deeds featured New Milford.
Drive over the steel bridge and head back towards Roxbury, turning left on Route 67 East.
From Route 67 East, turn right onto Route 172 South towards the South Britain historic district of Southbury. At the end of Route 172, Part 1 of this tour around colonial Litchfield area concludes.
You can choose to end your tour here, getting back onto Interstate 84, or continue on to Part 2 around the Lower Housatonic Valley River area for more rural country views.
Following the specific directions on the pdf here, venture into Southbury to take a peak at an expansive country horse farm located on the way to Kettletown State Park
Kettletown is located on the gorgeous tree-lined shores of the Lake Zoar fresh water reservoir, and it is a popular destination for campers.
Go for a short hike into the woods at Kettletown. Next drive over the town boarder into Oxford and stop off at Jackson’s Cove beach, also located on Lake Zoar.
Then continue onward to visit Stevenson’s Dam that forms the Lake Zoar reservoir. Drive over the dam to Monroe, and grab a hamburger at the burger joint on the lake.
Instagram famous shots
Go back over Stevenson’s Dam towards Oxford and take a right after the dam onto Route 34 East (Roosevelt Drive). Roosevelt Drive will take you on a parallel drive along the Housatonic River towards Derby.
Here you can see the houses from some popular Instagram and other social media photos such as this one from Jay Hagani’s Instagram and Flickr websites.
To get to this point of the river, look for McConney’s Farm, Greenhouse, and Bakery located in Derby at 795 Roosevelt Drive on the left side of the road. Either park your car here or up ahead of the road on a small gravel lot to the right. Walk to the curve in the road and look across the river to see the colorful leaves. Be careful of the traffic on the road.
Up ahead on Roosevelt Drive, look for the Gilder Boat House on right side of Route 34 East where the ivy league, Yale University crew team is based. You may just get to see the crew teams row on the river!
Here you have an option to end your tour. Continue driving along Route 34 East towards downtown Derby to pick up Route 8 and head on to either Interstate 84 towards Waterbury or the Merritt Parkway or Interstate 95.
Or take the option to backtrack along Route 34 West towards Seymour and Oxford. Take a right onto Route 188 North. Drive along Route 188 North to roundabout. Take the left to continue on Route 188 North into Oxford.
Route 188 will bring you through the historic Quaker Farms section of Oxford where you will see more vintage New England homes and churches.
Continue along Route 188 North, to Schreibers Farm (mentioned here in the New York Times) and stop there to go pumpkin picking, pet the farm animals and take a hayride around the farm.
The final stop on Part 2 of this tour is to Southford Falls State Park up ahead on Route 188. Take a break at the pond to feed the ducks and go for a short walk by the waterfall to the red covered bridge.
From Southford Falls, continue onto Route 188 North and take a left onto Route 67 North, following it back to Interstate 84 in Southbury. You have now completed the grand tour around western colonial Connecticut. Hope you enjoyed this road trip advenutre USA.
End of tour!
Download Embolden Adventures Connecticut Road Trip directions Here.
