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Fall in Connecticut! 10 Must-Visit Towns & Things to Do

ByKristen Valenti Updated on

Your guide to Connecticut this fall! From the rolling hills of Litchfield County to scenic suburbs around Hartford, there is so much leaf peeping to be had and quaint towns to explore. Here is your guide to see it all!

downtown salisbury connecticut with red leaved tree at fall lining the sidewalk.
Downtown Salisbury in fall ❤️
green grass with dog walking on trail surrounded by fall colored leaves in connecticut.
Platt Farm, Southbury 🍁
hill-stead museum with big white colonial and sidewalk and white fence surrounded by orange and yellow leaved trees.
Farmington museum, find it listed under Farmington below!🍂

Living in Connecticut almost my whole life, I love making the most of the fall season here. My favorite activity is seeking out scenic downtowns to stroll and explore, cafes to try, and local hikes and walks to admire the foliage. It makes for the perfect fall CT day trip!

In this post, you'll find 10 different quaint Connecticut towns and the best places to visit, hike, and eat in each town this fall.

  • kent falls waterfall with yellow leaves surrounding it.
  • outside juliens farmstore in fall with pumpkins outside and hill in distance.
  • hogpen hill farms sculpture park in fall with green grass and fall colored trees.

Whether you’re looking for wide open vistas to spy the leaves, cozy cafés with pumpkin spice lattes, or a place to simply wander and soak in the season, Connecticut has countless spots worth exploring.

So get cozy in the perfect fall flannel and check out some of the best CT towns to visit including suggestions for where to hike, eat, and explore in each town! 🥾☕️🍁

A Guide to Fall in Connecticut; 10 Must-See Towns

1. New Preston

  • downtown new preston in fall with white colonial storefront shop.
    Fall view at The Owl restaurant
  • downtown new preston in fall with white colonial storefront shop.
    Downtown New Preston
  • Lake Waramaug view from Meeker TRail
  • View from Meeker Trail
  • Fall meal at The Owl! 🦉

Nestled along Lake Waramaug, New Preston is a charming village that feels especially cozy in the fall. The small downtown is lined with boutique shops and antique stores, making it a perfect stop after a leaf-peeping hike.

It's the kind of town you can easily miss as yoou drive by if you don't know where to look! I love that it's tucked away. I suggest putting The Smithy Market in your GPS and starting here where you can walk and explore the little town.

  • Hike: Macricosta Preserve
  • Eat: The White Horse Country Pub
  • Cafe: The Smithy Market
  • Visit: Downtown New Preston and Hopkins Vineyard

2. Washington Depot

  • river at hidden valley preserve in connecticut in fall surrounded by green, red, and orange colored trees and blue skies above.
    Bee Brook Preserve
  • spring hill vineyards view from atop a silo with green grass and picnic tables below.
    Spring Hill Vineyard view
  • river at hidden valley preserve in connecticut in fall surrounded by green, red, and orange colored trees and blue skies above.
    Hidden Valley bridge
  • tray of apple cider donuts at averill farm in washington connecticut.
    Averill Farm 🍎
  • averill farm in washington connecticut.
    Averill Farm

Surrounded by rolling hills and scenic preserves, Washington Depot is an ideal fall destination for anyone who loves both nature and small-town charm. After all, this is the town that inspired the scene and setting of the Gilmore Girls show!

There are so many hikes to choose from in Washington from easy walks to longer trails. With such a scenic and cute downtown it's worth it to take a ride here just for lunch at The Pantry! But I would suggest heading to Hidden Valley Preserve after to cross Thoreau Bridge, or walk to the old train tunnel in Steep Rock. End the day by stopping at Averill Farm for an apple cider donut or Spring Hill Vineyard for a snack and glass of wine! 🙂

3. Litchfield

  • lawn and white colonial house at sunset with golden glow in the sky.
    Tapping Reeve Scarecrow Festival🎃
  • woman on a hike overlooking large lake lined with orange, red, and yellow trees.
    Trail at White Memorial 🥾
  • old historic white colonial house with red door in downtown litchfield surrounded by autumn colored leaves and trees.
    House along North Street❤️
  • two big black and brown dogs on a boardwalk over water with reflection of fall trees in bright blue lake in litchfield.
    Captain & Bauer at White Memorial
  • big blue bantam lake in litchfield surrounded by orange and brown leaves in late autumn in connecticut.
    Bantam Lake 💙

There's so much to see in Litchfield, making it a must visit for fall in Connecticut. I was lucky enough to live in Litchfield for several years and it jsut has it all from New England charm with the historic homes, buildings, and churches to the many cafes to choose from and tons of places to walk to take in the foliage.

My perfect fall day here would involve a stroll along North Street to see the colonial homes lined with pops of fall leaves, checking out the local shops along Main Street, coffee at Toast & Co., and a hike at White Memorial. Oh, and you must enjoy the seasonal scarecrow festival on the scenic meadow and yard at Tapping Reeve, the first law school in America!

There are lots of hikes to choose from in Litchfield so check out my post to pick the best one for you! ➡️ 10 Different Hikes in Litchfield, CT 🍁🌟

  • Hike: White Memorial
  • Eat: Marketplace Tavern (casual) or West Street Grill (special meal)
  • Cafe: Toast & Co.
  • Visit: Downtown Litchfield, North Street stroll, Scarecrow Festival at Tapping Reeve Meadow

4. Kent

  • kent falls waterfall with yellow leaves surrounding it.
    Kent Falls
  • counter at a bakery with a variety of baked goods behind the glass case and a chalkboard menu above.
    Wilson's By High Watch Cafe
  • woman in long sleeved blue shirt at the top of a hike in kent at caleb's peak with orange colroed leaves in the distance.
    View from Caleb's Peak
  • fuller pond in connecticut framed by red leaves.
    Fuller Pond
  • lake in Connecticut framed by orange and brown leaves.
    Fuller Pond 🍂

Another super charming town to visit in CT this fall! At the base of the Appalachian Trail, you'll find a scenic downtown to stroll with the hills in the distance and fall trees lining the streets. Downtown shops and galleries pair well with a hearty meal at Kingsley Tavern after a hike on the Appalachian Trail.

I wrote a whole post about what to do in Kent so before your visit check it out to better plan your trip! ➡️🌟 25 Things to do in Kent, CT 🍁🌟

  • Hike: Caleb’s Peak on the Appalachian Trail or Kent Falls
  • Eat: Kingsley Tavern for a special dinner or Wilson's for breakfast/lunch
  • Cafe: Wilson’s by High Watch
  • Visit: Downtown Kent

5. Granby

  • outside juliens farmstore in fall with pumpkins outside and hill in distance.
    Julien's Farmstore ☕️
  • brown dog on overlook in granby connecticut overlooking fall colored leaves below.
    Barndoor Hill hike
  • outside of juliens farmstore in granby with black two top tables and baked goods on table.
    Breakfast outside Julien's
  • clark farm sign in granby CT with blue sky above.
    Clark Farms 🎃
  • hand holding an apple cider donut in granby connecticut.
    Donuts at Clark Farms

There are so many reasons to visit Granby this fall, from vibrant vineyards to multiple farms. It’s the kind of place where you can spend a crisp afternoon hiking and then wind down with a glass of wine or cider.

My perfect fall day in Granby would involve a hike at McLean Refuge (love the Barndoor Hill trail), a stop at Julien's Farmstore for treat and coffee, a ride to Clark Farms for apple cider donuts (lots of kid activities here, too!) picking up produce at The Garlic Farm, and walking around Old Mill Pond Village to get in the fall and holiday spirit!

To plan your fall day in Granby and for more details on all the places check out my post: ➡️🌟 Visiting Granby, CT 🍁🌟

  • Hike: McLean Refuge Barndoor Hill Loop
  • Eat: The Bear’s Den or The Barn
  • Cafe: Julien’s Farmstore
  • Visit: Clark Farms, Old Mill Pond Village Shops, Lost Acres Vineyard

6. Simsbury

  • flamig farm in simsbury connecticut with red barn surrounded by orange leaved trees.
    Flamig Farm petting zoo!
  • outside of tulmeadow farm and red barn and mums in front.
    Tulmeadow Farm stands
  • brown barn with white writing saying Flamig Farm.
  • inside flamig farm store in connecticut in fall with table of egg cartons and local honey.
    Goodies inside Flamig Farm store
  • patch of green grass lined with pumpkins in front in simsbury connecticut in fall.
    Tulmeadow Farm trails

There is so much to do in Simsbury and it offers all the best fall activities —scenic hikes, farm visits, and some of the state’s best dining. Whether you’re walking through farmland or dining by the river, you’ll find plenty of ways to enjoy the season here.

  • Hike: Penwood Lookout or Hedgehog Mountain
  • Eat: Millwright’s Restaurant
  • Cafe: The Coffee Spot
  • Visit: Flamig Farm and Tulmeadow Farm

7. Southbury & Woodbury

  • green grass surrounded by fall colored leaves and mountains in the distance in connecticut.
    Platt Farm trail early morning 🍁
  • green grass surrounded by fall colored leaves and mountains in the distance in connecticut.
  • large stone sculptures at hogpen hill in connecticut.
    Hogpen Hill
  • hogpen hill farms sculpture park in fall with green grass and fall colored trees.
    Hogpen Hill

These neighboring towns combine scenic beauty with cultural treasures. Fall is the perfect time to hike through peaceful trails and then spend the afternoon at a unique sculpture park.

  • Hike: Platt Farm Trail
  • Eat: 1754 House
  • Cafe: AM Coffee and Co
  • Visit: Hogpen Hill Farms Sculpture Park

8. Salisbury

  • house at dusk with golden lights shining from within with a spooky vibe and orange leaves all around.
  • rands view overlook with green grass, hills in the distance, and orange trees dotting the landscape.
    Rand's View
  • downtown salisbury connecticut with red leaved tree at fall lining the sidewalk.
    View of Sweet William's Cafe
  • connecticut lookout with golden and brown leaved trees in the distance at sunset time with golden sky.
    Salisbury Land Trust hike
  • downtown salisbury connecticut with red leaved tree at fall lining the sidewalk.
    Downtown Salisbury
  • rands view overlook with green grass, hills in the distance, and orange trees dotting the landscape.
    Rand's View 🍁

Tucked in the northwest corner of the state, Salisbury feels like stepping into a classic New England postcard. With mountain views, charming shops, and delicious dining, it’s a must for a fall day trip.

  • Hike: Rand's View
  • Eat: Woodland
  • Cafe: Sweet Williams
  • Visit: Downtown Salisbury Shops

9. Farmington

  • hill-stead museum with big white colonial and sidewalk and white fence surrounded by orange and yellow leaved trees.
    Hill Stead Museum grounds
  • hill-stead museum with big white colonial and sidewalk and white fence surrounded by orange and yellow leaved trees.
    Hill Stead Museum grounds🧡
  • hill-stead museum with sidewalk and white fence surrounded by orange and yellow leaved trees.
    Hill Stead Museum grounds💛
  • two women and two dogs sitting on edge of pinnacle rock hike in connecticut during fall
    Pinnacle Mountain
  • amazing fall hike view at sunset time in connecticut with red leaves framing the photo
    Pinnacle Mountain at sunset
  • silhouette of woman and black dog on pinnacle rock in farmington connecticut
    Pinnacle Mountain

Farmington blends history and scenery, making it a perfect fall stop. From walking the grounds of Hill-Stead Farm to hiking up Rattlesnake Mountain for sweeping views, there’s something here for every type of fall adventurer.

  • Hike: Rattlesnake Mountain
  • Eat: Naples Pizza or Fork n Fire
  • Cafe: Hartford Baking Company
  • Visit: Hill-Stead Farm

10. Collinsville

  • woman with brown hair in green flannel on overlook at sunset time with soft pink and blue skies.
  • woman with brown hair in green flannel with black dog on overlook at sunset time with soft pink and blue skies.
    Sweetheart Mountain at sunset 🌕
  • full moon in pink sky on a hike in collinsville connecticut.

This artsy riverfront village is one of Connecticut’s hidden fall gems. The historic downtown is full of character, and with nearby trails and riverside paths, you can easily spend the whole day exploring.

  • Hike: Sweetheart Mountain or easy walk on the Farmington Canal
  • Eat: Lasalle Market
  • Cafe: Giv Coffee
  • Visit: Downtown shops and center

I hope you enjoyed this post all about visiting CT this fall and found some gerat inspiration for fall in Connecticut here!

Get out your calendar and plan away - you will fall in love with each town on this list.

Enjoy and happy fall!! 😍💗🥾

Continue to get in the fall mood by checking out another fun fall post ➡️ my Top 5 Women's Flannels; Tested & Reviewed!🌟

brunette woman on a fall day in vermont with orange leaves on the ground wearing an oversized green flannel jacket with hands in the flannel's pockets.

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