Things To Do In CT In October: Top 23 Most Unique Picks | Stanton House Inn
A fall foliage trip to Candlewood Lake is one of the best things to do in CT in October

Things to Do in CT in October: Top 23 Most Unique Picks


Fall foliage in the woods of ConnecticutWhen most people think of Connecticut, they think of yacht clubs and Yale University. However, when autumn arrives, the union’s third-smallest state has much to offer.


Stay in Connecticut to experience a true New England autumn and the many things to do in CT in October. Everyone else will be stuck in traffic, driving to upper New England. So, you can laugh at them while you enjoy an apple cider doughnuts under the apple trees.


Connecticut, with a total area of 5,543 square miles, is easy to explore. Due to its size, the “Constitution State” manages to cram a wide variety of exciting, tranquil, and historical locations into a small, easily navigable space.


Connecticut is one of the best places to see fall foliage near New York City. It has the longest season in all New England, after all. That said, Connecticut has more to offer than just viewing the fall foliage.


The state’s charming and historic B&Bs, scenic byways, and fall festivals make it easy to immerse yourself in the fall season for a quick (or extended) visit.


Read on for your fall bucket list:


Celebrate Halloween and the harvest season


A pile of pumpkins for sale during October in ConnecticutNew Englanders love Halloween and the harvest season—and this New Englander is no different.


Here are some of the best activities to do in fall in CT!


Pumpkin patches

Is there anything more classically Connecticut than pumpkin picking? Go to your favorite pumpkin patch, pick your own perfect pumpkin, and bring home your bounty!


There are numerous pumpkin patches on Connecticut farms with pick-your-own apples, hayrides, and corn mazes that make you feel like a kid again.


Some favorites include:

  • Bishop’s Orchard in Guilford, CT
  • Lyman’s Orchard in Middlefield
  • Wicked Pumpkin Orchards in Willington
  • Silverman’s Farm in Easton
  • Johnny Appleseed in Ellington
  • Holmberg Orchards in the Gales Ferry neighborhood of Ledyard, CT

Apple orchards

Most equate autumn in New England with apple picking, and fortunately for them, the soil and weather in Connecticut during these months are ideal for apple orchards.


The apple-picking season typically lasts from mid-August to early September, depending on the orchard, with most visitors arriving in late September.


The Constitution State hosts a wide variety of orchards. Lyman Orchards is a popular and well-known farm. Since John and Hope Lyman purchased the 37 acres of land where the current Homestead resided in 1741, Lyman Orchards has become a common name on “top 10” lists.

pick your own apple orchards in ct Things to Do in CT in October: Top 23 Most Unique Picks
Map design by Stanton House Inn with resources from Flaticon

Corn mazes

Exploring Connecticut corn mazes is one of the more charming (and less difficult) ways to enjoy October.


The Connecticut corn maze tradition takes advantage of the harvest season, using corn fields at the end of the growing season.


A corn maze is a novel and energizing way to explore Connecticut’s winding countryside.

connecticut corn maze map Things to Do in CT in October: Top 23 Most Unique Picks
Map design by Stanton House Inn with elements from Flaticon

Haunted Places

Skeletons for sale during the Halloween season

Finding your first stop on a road trip to explore Connecticut’s most haunted places will not take you far.


The state has received numerous reports of ghost sightings. And Connecticut being such a small state helps, as well.


We have a list of 23 of the scariest haunted places to visit in CT, so don’t miss out on the Halloween spirit.


If you’re someone who doesn’t like to be spooked, don’t worry about it! Go with your boo 😉 and get cozy together as you walk along what could be a haunted site.


One of the top cider mills, a great thing on the list of things to do in CT in October


CT cider mills are replacing craft beer and distilleries as a growing phenomenon returning to Connecticut.


By returning, I mean that apple cider was the first uses for all those apple trees planted throughout the Northeast. It was our first local hooch.


The New England Cider Co.’s autumn flavors include ciders with cranberry and pumpkin infusions.


Spoke and Spy Cider, one of the most unique cider makers, offers a chai-inspired cider that is ideal for a crisp autumn day. Or visit Yankee Cider Company, which specializes in New England-style hard cider that is drier and lower in sugar.


Whether you’re a beer connoisseur or a casual drinker, the variety of options available at Connecticut breweries will astound you. At the state’s more than 100 establishments, you can find everything from award-winning brews to small-batch craft beers.


Spend a crisp autumn day sipping a cold IPA at Kent Falls Brewing Company in the town of Kent, sample some “aggressively laid-back” brews at Stony Creek Brewery in Branford, CT, along the Branford River or unwind with a beer at Bank & Bridge Brewing in Mystic.


Read about the best breweries in Connecticut to find your new favorite spot!


Connecticut’s rocky soil and cold winters don’t vibe with stereotypical wine growing. That said, Connecticut is one of the fastest-growing wine regions in the world.


Pick anything from our list of the top Connecticut wineries on the CT wine trail to plan a weekend getaway to visit!

Fall foliage

Seeing the fall foliage is a great reason to visit CT


If you’re visiting from early October to November and want to enjoy the fall foliage, hop in your car, and take a drive through history.


There is nothing like the fall foliage in New England, no matter where you are in Connecticut. What truly distinguishes the area is the sheer number of tree species that produce a rainbow of colors in the fall.


Although there are several scenic fall foliage driving routes where you can see some of the best colors, going outside on foot is the best way to see them. Bear Mountain, the state’s highest point, and the Jessie Gerard Trail, which provides sweeping views of thousands of acres of forest, are two of the best hikes to enjoy the state’s fall foliage.


And Gillette Castle is a great destination any time of year. That said, the hills along the Connecticut River Valley, swatched in fall colors, is splendid from its vantage point.




CT Fall Foliage Driving Routes 2023 Things to Do in CT in October: Top 23 Most Unique Picks
Map design by Stanton House Inn

Day trips

A country road in Connecticut, covered with fallen leaves


Greenwich, Litchfield, New Haven, and Essex are some favorite Connecticut towns to visit in the fall. Enjoy the scenic drives as you travel to these classic New England towns, which are beautifully decorated with fall foliage.


Some of our favorite CT day trips include:



Posh Greenwich is a fall destination in its own right. And, being the farthest south, it also enjoys its burst of fall foliage last in the state.


So last-minute planners should head here.


Aside from its year-round attractions, especially:


Some more spots to visit in town ideal for a visit to Connecticut in October include:

Greenwich Audubon Center

The first of Connecticut’s top fall attractions is the Greenwich Audubon Center. It encompasses 686 acres of diverse habitat.


The nature reserve is home to many birds, but it’s also a beautiful place to visit in the fall when the leaves begin to change color.

Babcock Preserve

The next stop is the Babcock Preserve, a nature preserve with stunning fall foliage.


Hiking, picnicking, and birdwatching are all permitted and encouraged on the 300-acre property.

Mianus River State Park

Mianus River State Park is the final place in Greenwich to visit in the fall.


The trees at Mianus River State Park bloom in brilliant colors in the fall, and it’s a great place to see bald eagles that live along the river.


The 389-acre park offers mountain biking, hiking, and fishing.


Because dogs are allowed, it is also a popular destination for pet owners and their four-legged companions.

Litchfield County

Litchfield Hills, Connecticut—the fancy name for the county surrounding the town of Litchfield, Connecticut—has the best fall foliage.


According to rumors, this area inspired Amy Sherman-Palladino to create the coveted TV show, Gilmore Girls.


Hot air balloon rides, state parks, and farms are just a few of the fall activities available here.

Topsmead State Forest

Hiking in Topsmead State Forest is one of the best fall activities in Connecticut near Litchfield.


If you come here for a hike or a picnic during peak season, you can spend the day surrounded by the most vibrant colors.


These hikes are classified as easy because their lengths range from 0.5 miles (Bernard Stairs Trail) to 1.5 miles (Songbird Trail).


The area was given to CT residents after owner Edith Chase died in 1972.


Today, Topsmead remains top of the list of free places to go in Connecticut.

White Memorial

White Memorial is the state’s largest privately owned conservation area.


Alain and May White founded the 4,000-acre park in the hills of northwest Connecticut in 1913. It has over 50 entrances and 40 miles of trails winding through fields, wetlands, and forests.


The most well-known trail is the Little Pond Trail, also known as the Boardwalk Trail. It is a 1.2-mile wooden bridge spanning the Bantam River.


The park includes ten ponds, Bantam Lake Shoreline, Apple Hill, Catlin Woods, and White Memorial’s Point Folly Marina.


Julia Roberts made the small town of Mystic famous for her role in the film Mystic Pizza, which is based on a local pizza shop. There are many more reasons to visit Mystic than a 1980s movie—as lovely as Julia Roberts is.


The Jealous Monk’s 32 rotating taps allow you to create your own Oktoberfest. For added effect, scarecrows are arranged along the walkways of Olde Mistick Village for the entire month of October.


Don’t miss B.F. Clyde’s Cider Mill, a national landmark and the oldest steam-powered cider mill in the country that has been open since 1881. After some exploring, if you order the donuts, you will not be disappointed.

Outdoor activities

Taking pictures with a pumpkin spice latte in one hand and a pumpkin in the other is nice.


But I prefer to be a bit more active while enjoying Connecticut in October.


Hiking to see waterfalls is one of the best choices for things to do in CT in October


Being on foot is one of the best ways to explore Connecticut’s beautiful state parks.


The crisp autumn air is ideal for a brisk hike through one of the state’s protected natural areas to observe wildlife and enjoy the scenery.


State Parks

Considering their sizes, you could lump more than a few of the top state parks across Connecticut into one day.


It’s not to say that’s an easy thing to do—as a few hikes might be exhausting, fair warning—but totally doable.

Talcott Mountain State Park

Climbing Talcott Mountain overlooking the town of Simsbury, CT, will give you the best views of the surrounding area.


After reaching the top, you can take a tour of the Bavarian-style tower, which was once a vacation home.

Devil’s Hopyard State Park

Explore the 1,000 acres of blissful autumn scenery at Devil’s Hopyard State Park in East Haddam. This stunning location’s peaceful picnic areas, hiking and biking trails, and fantastic fishing spots will appeal to everyone.


With a name like this, October would be the ideal time to be here.

Mount Tom State Park

Mount Tom State Park in Litchfield is another excellent location for hiking and leaf peeping. It is one of the state park system’s oldest parks, having been established in 1915.


Fun fact: Mount Tom’s summit rises 325 feet above sea level!


The stone lookout tower, one of the park’s hikes, provides spectacular views of the foliage. But don’t be discouraged if you’re not much of a climber: The trail is just 500 feet above sea level and less than a mile long.


Don’t miss our full list of top CT hiking trails before you head out.


Why not take advantage of Connecticut’s numerous bike trails? Biking along any scenic route from one end of the state to the other is a great way to take advantage of the autumn turn of the great outdoors.

Norwalk River Valley Trail

The Norwalk River Valley Trail connects the Long Island Sound at Calf Pasture Beach up to Danbury. It passes by many of the best attractions in Norwalk before meandering through the woods in:



  • Redding, Connecticut


Pequonnock River Trail

The Pequonnock River Trail runs 14 miles through Fairfield County, beginning in Bridgeport and ending in Newtown.


Because it follows the route of the former Housatonic Railroad, you will see state landmarks like the Beardsley Zoo and charming southern Connecticut towns before your journey ends.

Farmington Canal Heritage Trail

The Farmington Canal Heritage Trail begins at Yale University in New Haven, Connecticut, and travels through Hartford County.


The Farmington River Trail, the New England Rail-Trail Spine Network, and the East Coast Greenway all share its path, making it Connecticut’s longest paved bike path.


Some of the cutest towns you’ll pass through here include Avon, CT; Simsbury, Connecticut, and Farmington, CT.

Air Line State Park Trail

The Air Line State Park Trail runs nearly 55 miles through Middlesex, New London, Tolland, and Windham counties. Its southern trailhead is in the town of East Hampton, CT.


Ballast, gravel, and crushed rock cover the trail that links the 3,000-mile East Coast Greenway from Maine to Florida with the New England Rail-Trail Spine Network.

Enjoy a scenic train ride on the Essex Steam Train & Riverboat

Since 1868, the Valley Railroad Company has been a beautiful feature of Connecticut’s landscape. Daily train and boat excursions are available, both offering interesting experiences.


You can also participate in the “Boos, Brews, and BBQ” annual event, where professional ghost hunters will lead guests on a spooky tour of the station grounds.


Hocus Pocus’ Sanderson Sisters visit Essex, CT, on The Salem Express for a fun family outing. Just watching the steam train in action is a real treat, even if you don’t take a ride (which is highly recommended!).


For a thrill, 180 platforms have been installed on Adventure Park‘s “treetop trails” and are ready for exploration!


Although ziplining is not for everyone, it is very safe for adults and children ages five and up. These lines provide a bird’s-eye view of all the changing foliage colors in Storrs.


If you’re not afraid of heights, ride across Farmington Valley and the Litchfield Hills in a hot air balloon ride.


Berkshire Balloons takes off from New Hartford and gives a perfect aerial view of Connecticut.

Kayak foliage tours

There is a 500-acre canoe and kayak trail in the Connecticut River Estuary. Travel the waterways through seemingly endless routes to explore and get in shape this fall.


Share a picnic before or after kayaking for as long as you want on the water. Kayaks, canoes, and paddleboards are easily accessible to experts and novices alike for trips to the CT shoreline and CT beaches only accessible by water.

Fall festivals across Connecticut in October

Woman enjoying caramel apples, ideal for a sweet tooth, at one of the best fall festivals in CT that's fun for the whole family


The month of October is jam-packed with events, festivals, and activities.


CT has something for everyone this season, including:

  • Lavish food festivals for delicious food, like the perfect apple pie
  • World-class musical performances with plenty of live music
  • Numerous historical and cultural activities for family fun
  • A harvest festival or two


Not sure where to begin?


See our list of the best Connecticut fall festivals. It has all our favorite fall festivals. Getting to at least one fall festival this year is worth the effort!

Halloween-themed events and haunted attractions

If you’d rather something a little less real than an actual haunted house, you’ll find plenty of the more creative kinds throughout the state.

Phantom Fall Fest at Lake Compounce

In Bristol, Connecticut, the infamous Phantom Fall Fest festival is held at Lake Compounce. While you may enjoy the more autumnal side of October versus spooky, haunted houses are part of the annual Halloween celebration.


The park is open without its scare factor during the day for families and scaredy-cats, but once the sun sets and the lights go out, it transforms into your worst nightmare.


Every evening, new scares and special effects are added to the experience. Even though actors roaming the room cannot touch you, they may approach you closely to scare you.

Harvest festivals and fairs

Celebrating the harvest season is a longstanding tradition in most cultures.


And Connecticut and its local farmers, especially, are no different.

Highland Games Festival

The Highland Games are one of Connecticut's fall bucket list items


The small town of Scotland and the country share more than just a name: The Connecticut Highland Games Festival is also held here.


You don’t have to hop on a plane and spend a fortune to see some men in kilts. Every year in early October, a large festival welcomes anyone who enjoys caber tossing and step dancing to join in the fun.


A fiddler’s workshop, a “bonnie knees” competition, herding dog demonstrations, and some traditional harp playing are some of the additional events and activities.


Scarecrow festivals

There are no yellow brick streets in Old Wethersfield. What you will find, however, is a plethora of hand-crafted scarecrows created by local artisans, families, and store owners. The scarecrows that line the streets range from creepy to downright amusing.


Scarecrows in the Meadows is another Litchfield attraction. Locals are invited to view over 50 scarecrows and vote for their favorites every year.

Connecticut Garlic & Harvest Festival

Every October, the Connecticut Garlic & Harvest Festival happens in Bethlehem. It features a plethora of free samples, live music, and numerous cooking demonstrations featuring garlic. If you enjoy all things garlic, you should definitely check it out. You might be overwhelmed by the garlicky cheeses, spreads, and dips.

Or not.

Renaissance Faire

Before heading to the Connecticut Renaissance Faire, grab your nearest sword and rewatch every episode of Rings of Power.


Or The Witcher.


Or Game of Thrones.


You get the vibe.


The Renaissance Faire, which usually starts in early September and lasts until mid-October, is great for everyone who enjoys a unique adventure. The mead doesn’t hurt either.


The Knights School, where children can train to become squires or full-fledged knights, will be popular with kids. While we’re on the subject of fledging, check out the acrobatic flights of the Knightwings, or birds of prey. The traditional jousting tournament, in which knights compete for the hand of a fair maiden, is a wonderful way to end the day. You can check their website for the theme of the weekend to plan your costume.

Indoor activities in October

Rainy day in October? No problem! There are plenty of indoor activities to keep you and your family entertained in Connecticut.


There are tons of typical indoor activities across Connecticut:

  • Connecticut museums and art galleries
  • Live theatre and music performances
  • Aquariums, like the Maritime Aquarium
  • Head to a movie theatre


But there are a few things that feel more special and specific to Connecticut in October.


Apple pie


Connecticut is no longer just a place to see the fall colors—it has become a lesser-known foodie destination with award-winning restaurants and chefs.


Need some ideas?


Check out our guide to the most romantic restaurants across Connecticut for somewhere near you.


Woodbury, Connecticut, has earned the moniker “antiquing capital” for good reason. A town in Litchfield County, Woodbury has developed a reputation as a center for antique shopping over the last fifty years, thanks to businesses gathered around Main Street’s historic homes.


Woodbury has become a popular stop for antique shoppers since then. Most of the eleven stores, which sell everything from fine art to vintage wedding gowns, are located on Route 6 along a three-mile stretch of Colonial and Victorian homes.


State legislation has designated several towns, including Woodbury, as part of the “Antiques Trail” by state legislation.


Because that was of course the most important thing for our legislators to be doing.


From high-end antiques to flea markets, Connecticut antique shops along the trail have a little bit of everything. The trail is ideal for both sightseeing and antiquing. The trail is a great way to see Connecticut because it winds through Hartford, Fairfield, and Mystic Country.

Keep discovering more things to do in CT in October

Taking roadtrips along CT highways is one of the best things to do in CT in October


Any time of year is a good time to visit Connecticut.


However, Connecticut has a special ambiance in the fall that makes it unbeatable for tourists. So, why miss out?


October gets all the attention, but be sure to read our guides to the other autumn months:


I’m also quite partial to the Hudson River Valley, next door in New York State. A drive up the valley to Highland, NY, and other spots in Ulster County is an annual must-do on my list.


Or, read our guides to the summer months in Connecticut:

And remember to check out our complete guide to the best fall sights, events, and activities in Connecticut.


We hope you enjoy your next adventure!

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