Ultimate 3-Day Connecticut Fall Foliage Road Trip Itinerary (New England Hidden Gem!)

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If you are looking for a fall foliage itinerary without all the crowds, I’ve got a suggestion that might just surprise you: Connecticut. Yes, really!

While it’s often overshadowed by its more famous neighbors like Vermont, New Hampshire and Maine (and I myself love these places!!!) Connecticut offers a spectacular autumn palette that can rival any in New England.

Every time I have done a New England fall foliage trip, I have found that Connecticut is my favorite. It is home to my favorite cider mill, it has less crowds and the foliage hangs around much later than other places so if you need to take your trip later in the fall season, this is the place for you!

Its charm is quieter, sure, but every bit as vibrant. So grab your favorite flannel and let’s dive into a three-day fall foliage road trip in Connecticut.

When considering a Connecticut fall foliage road trip, just picture this photo: a white, historic house, whose huge windows look out over the golden yellow leaves of a tall tree.

When To Take This Fall Foliage Road Trip

The best time to take a fall foliage road trip…..changes ever year! I know this isn’t what you want to hear, but it is the truth!

There are great fall foliage prediction maps that you should check out! These change every year, so wait until it updates for this year, and then use it as a guide. Of course, this is just a prediction and things can change, but it is a good guide to check!

Connecticut is GREAT if you are later in the season and want to plan your fall trip! I recommend the second or third week of October for the best results on this Connecticut trip.

I usually go around October 15-23. That is my usual range year over year.

That being said, IT CHANGES!! Check the predictions, but keep in mind they are just that, predictions!

But I would say you are pretty good to go if you are planning to visit in the second or third week of October! You won’t regret it!

holding a cup of iced apple cider and cider donuts

Getting There & Getting Around

I recommend flying into either Boston or Hartford. I have done both. I recommend just doing whichever is more affordable to you. If you go from Boston, it will be a 2 hour drive which does cut into your time, so keep that in mind!

I love Hartford, it is a smaller airport than Boston but still has affordable flights and lands you right in Northern Connecticut.

Renting a car is your best bet for this trip, giving you the freedom to explore the quaint corners and curvy backroads of Connecticut at your own pace. You must rent a car to be able to do this Connecticut fall foliage itinerary.

A long road stretches ahead of the viewpoint of a camera, yellow and orange trees surrounding the highway and above a black car as it travels.

Day 1 & 2: Fall Foliage In Northern Connecticut

For Day 1 and 2 I recommend staying at the same place in Northern Connecticut. You will be able to easily drive around to all of these spots and it is one less place to move your luggage from to maximize your time seeing the incredible fall foliage.

Let’s get started exploring my favorite fall stops in Connecticut!!!!

During a Connecticut fall foliage road trip, don't be surprised to see the literal fall foliage on the ground, yellow and orange and brown and red leaves scattered on the roads.

Stop 1: Hogan’s Cider Mill

Start your trip with a taste of local tradition at Hogan’s Cider Mill in Burlington. Sip on some crisp, freshly made cider and don’t miss trying their hard ciders if you’re in the mood for something with a bit more kick.

I recommend their cider topped with a cider donut and whipped cream! It is only served on certain days of the week so make sure to call ahead if you want to be 100% sure!

I always grab donuts and a pint of cold apple cider to go so I can enjoy during my trip!

A close up of a cup of cider topped with a donut and whipped cream is eye catching in yummy: in the foreground is a blurry red pick up truck that also has crates of pumpkins around it.

Stop 2: Castle Craig

Next up, head to Castle Craig in Meriden. Towering above Hubbard Park, this stone observation tower offers jaw-dropping views of the fiery foliage below. It’s a perfect photo op spot, so keep your camera handy!

This place is super unique and the foliage in the valley is gorgeous! Make sure to check the closing times as the road up there is not open all day!

During a Connecticut fall foliage road trip, make sure to check out Castle Craig , which is a tower that looks over the fire foliage below. It is a beautiful, stone observation tower.

Stop 3: Lost Acres Orchard

Lost Acres Orchard in North Granby is a total local favorite if you are looking for a hidden gem. They have tons of baked goods but my favorite that I highly recommend is the Mile High Apple Pie.

If you can only get ONE pie on your trip [as they are $$$] I would wait until Day 3 as that is my favorite cider mill in all of New England!

If you want to buy 2 pies and have the budget [I do this..I am not afraid to admit!!] Then try the mile high apple pie!!

A woman in a red dress holds an apple cider donut in front of the Lost Acres Orchard sign, which is full of fun, local fall things to do.

Stop 4: Marvel At The Connecticut Homes

Also, the homes in Connecticut are STUNNING!!!!! Some of the best I’ve seen and I think the prettiest in all of New England. I love just driving along or walking along and enjoying some of the beautiful homes blanketed in the best fall foliage!!!!

A white, historic home with dark shutters and big windows takes up the background of this photo and yellow, bright leaves on a tree-- which are the iconic symbol of a Connecticut fall foliage road trip-- hangs from the left corner.

Connecticut Day Trip Options:

I LOVE Northern Connecticut there is so much to see and do!!! But just a short hour drive away in Massachusetts there are even more cool things!!! Here are some of my personal favorites!

Emily Dickinson Museum: Literature lovers can take a short drive to Amherst, Massachusetts, to visit the home of one of America’s most beloved poets. It’s a serene spot that seems straight out of a storybook during the fall. I loved the tour here!

A woman in a black dress holding a lantern, stands in front of the home of Emily Dickinson, whose house is two story with green shutters and yellow paint.

Basketball Hall of Fame: Sports enthusiasts aren’t left out! The Hall of Fame in Springfield, Massachusetts, is an easy drive and a fun way to spend a few hours. I did both of these on the same day as you pass right by the Hall Of Fame on your way to Emily’s house!

During a Connecticut fall foliage road trip, don't be afraid to swing by the Basketball Hall of Fame: this photo shows the intro of the museum with it's huge dome and court-inspired decor.

More Fall-Themed Activities In Northern Connecticut

Don’t miss out on some quintessential fall activities:

Fall Foliage Cruises on the Connecticut River: Take a scenic fall foliage cruise from Hartford down the Connecticut River. Companies like RiverQuest offer sightseeing cruises that highlight the spectacular autumn colors along the riverbanks.
Hiking and Biking: Take advantage of the cooler weather to explore some trails. Penwood State Park, located in Bloomfield just a short drive from Hartford, offers excellent trails for hiking and mountain biking with beautiful overlooks to view the changing leaves.
Heublein Tower in Talcott Mountain State Park: A moderate hike up to Heublein Tower offers panoramic views of the Connecticut landscape ablaze in autumn colors. The tower itself is historically significant and offers a glimpse into local history.

The Heublien Tower in Talcott Mountain State Park is tall with grey stone, and red lining: this observation tower overlooks and offers great panoramic views of foliage.

Where to Stay in Northern Connecticut:

The Simsbury Inn – A quaint hotel with cozy rooms perfect for chilly fall evenings.
Avon Old Farms Hotel – Set in a beautiful, pastoral landscape, this hotel offers comfort and classic New England charm.
Residence Inn by Marriott Hartford Avon – Located in Avon, this hotel caters to guests looking for extended stays with studio, one- and two-bedroom suites equipped with kitchens. Amenities include free breakfast, a fitness center, and an outdoor pool.
DoubleTree by Hilton Hotel Bristol – Situated in Bristol, to the west of Hartford, this hotel features comfortable rooms, an indoor pool, and an on-site restaurant. It’s also close to the ESPN headquarters and the New England Carousel Museum.

A winding, grad staircase with gold accents sits in the lobby of the Avon Old Farms Hotel, which is a great place to stay during a Connecticut fall foliage road trip. — Avon Old Farms Hotel via Booking.com

Day 3: Coastal Charm in Mystic

For your last day, head down to Mystic, Connecticut. This place seems like it is out of a Hallmark Movie or the set of Gilmore Girls!!!!

A woman in a yellow hat and a green-leaf sweater holds a huge yellow leaf next to her head while grinning.

Stop 1: B.F. Clyde’s Cider Mill

Kick off your last day at my personal favorite, B.F. Clyde’s Cider Mill in Mystic. This is the oldest steam-powered cider mill in the U.S., and their cider, both hard and soft, is the stuff of legends. Watching the cider-making process here is truly a unique experience.

There may be a long line but it is worth it. The baked goods and ciders are the best in all of New England [and I stop at a lot of cider mills….for science of course ;)]

You WILL NOT regret a stop here, it is incredibly worth it, best apple pie in New England and everything is a 10/10!

A woman in a red skirt and a mushroom sweater holds onto cider and donuts in front of a Cidermill, which is a great foodie stop!

Stop 2: Explore Mystic

Spend your afternoon exploring the delightful coastal town of Mystic. Here are some of my favorite things to do!!!!

Mystic Seaport Museum: Explore America’s leading maritime museum. The Seaport Museum is home to a recreated 19th-century seafaring village, historic ships (including the last wooden whaleship in the world, the Charles W. Morgan), and a working preservation shipyard. It’s a must-visit for anyone interested in maritime history.

During a Connecticut fall foliage road trip you may want to check out the Mystic Seaport Museum, which is on the coast and is noticeable with its entrance because there is a huge anchor in front of the stairs! — Photo Credit: Singh_lens via Shutterstock.com

Downtown Mystic: Stroll through the picturesque historic Downtown Mystic, known for its drawbridge (Mystic River Bascule Bridge), unique shops, and excellent eateries. Be sure to stop by the Mystic River Park to watch the bridge rise for passing boats.

A woman on a pier looks over the water and at the draw bridge of downtown Mystic. Her hair is down and she wears a bright red dress that contrasts the blue of the water and town.

Olde Mistick Village: Experience shopping in a recreated 18th-century New England village setting. Olde Mistick Village boasts a unique collection of boutiques, specialty shops, and dining options. It’s a great place to find local handicrafts, jewelry, and souvenirs.

Mystic Pizza: Foodies and film buffs alike will enjoy a visit to the famous Mystic Pizza, the restaurant that inspired the 1988 movie of the same name starring Julia Roberts. Try a slice of their well-known pizza and soak up the nostalgic atmosphere.

A close up shot of the Mystic Pizza sign-- yes inspired by the movie starring Julia Roberts-- reads "A slice of Heaven."

Optional Day Trip to Newport, Rhode Island:

If you’ve got extra time, a one-hour drive to Newport is well worth it. Tour the famous mansions decked out in gilded-age splendor, stroll along the Cliff Walk for ocean views, and maybe catch a late lunch at one of the harbor-side restaurants.

A woman in a yellow skirt and a fall-leaf sweater stands in front of the cute shops of downtown mystic during a Connecticut fall foliage road trip.

I LOVE Newport and highly recommend seeing the Breakers Mansion if you can!! Of course, this is just an optional day trip as there is plenty to see in Connecticut.

If you visit Newport, make sure to stop at the KJP flagship store in downtown! It is where I get all of my cute fall-themed sweaters [well, I get them online, but the store is SO cute!]

A women smiles in front of the MJP store, wearing a classic fall-inspired sweater from here: the yellow and orange leaves on the sweater mass the foliage of a Connecticut fall foliage road trip.

Where to Stay in Mystic:

The Whaler’s Inn – Located right in downtown Mystic, this charming inn is walking distance from everything.
Mystic Marriott Hotel & Spa – For those looking for a bit more pampering, this hotel has all the upscale amenities.

A close up of the Whaler's Inn sign points guests to the lodging in Downton mystic that is close to everything: the blue sign, white lettering and anchor are truly coastal.

As you wrap up this foliage-filled getaway, whether you’re driving back to Boston or catching a flight from Hartford, you’ll leave with a camera full of photos and a heart full of autumn.

Of course, if you have longer than 3 days, you are welcome to spend as long as you want exploring fall foliage in Connecticut!! I have spent up to 10-14 days in this area and it is incredible every time! I discover new hidden gems and fun things to do with each visit, and it isn’t nearly as crowded as New Hampshire or Vermont!

A women dawning a long grey dress and a white-long sleeved shirt underneath calls back to historic times while she holds a straw basket and stands on a street that is full of leaves during a Connecticut fall foliage road trip.

Connecticut might just become your go-to for those fall vibes. Trust me, it’s worth veering off the beaten path!