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Fall in Litchfield County; Must-See Spots, Drives, & Hikes!

If you’re looking for the best places to experience fall in Litchfield County – you’re in luck! I’ve got a local’s guide (that’s me!) to the best drives to take, farms to visit, must-visit scenic spots, hikes, and more. ๐Ÿ๐ŸŽ

This post includes: top 10 scenic places to see the foliage (easy views), done for you day trip itineraries, 6 different hikes, 5 not-to-miss towns, and 3 scenic drives!

big red barn with red silo in fall with american flag on the barn and pumpkins out front.
Find multiple farms to visit on this list! ๐ŸŽ๐ŸŽƒ
woman on a hike overlooking large lake lined with orange, red, and yellow trees.
Our favorite fall trail at White Memorial ๐Ÿฅพ
man with backpack walking down trail in fall with two big black dogs in litchfield connecticut.
Flat trails to walk & enjoy the foliage ๐Ÿ

In the hills of Litchfield County, you never know what pretty view is around the corner and this is especially true in fall.

Tucked into the northwest corner of Connecticut, this region is filled with mountains, quiet country roads, and historic towns that are exceptional with a fall backdrop!

I lived in Litchfield for several years, and even though I live outside of town now, I still take the short drive here often.

This area always makes me feel like I’m on vacation – far away from the busier towns of CT. It’s a local escape and the perfect destination for fall in Connecticut as the hills in our state alight with color.

Bigger hikes if you want an elevated view of the leaves!๐Ÿ
Main path at Topsmead Park

This guide has the best spots in Litchfield County no matter the season!

And if you are completely new to the area, I’ve got done for you day trip itineraries further in the article so you don’t have to worry about planning and wasted time driving around!

Whether youโ€™re looking for scenic drives, apple and pumpkin picking, charming town centers, trails, or places to pull over and take photos – Litchfield County checks all the boxes!

Let’s dive into the best places to visit across Litchfield County this fall! ๐Ÿš˜๐Ÿโ˜•๏ธ And if you’d like to learn about the area more check out more helpful posts below! โฌ‡๏ธ

The West Cornwall Covered Bridge is the longest covered bridge in Connecticut and one of the most picturesque spots in the the whole state! The bright red bridge stretches 162 feet across the Housatonic River and is so picturesque in the fall.

I suggest parking and walking on the grass along the river, snapping photos or taking in the scene. Visit early morning for a chance of fog rising from the river which makes it feel even more like fall!

You can drive through the bridge as well, one car at a time so take it slow and wait your turn. ๐Ÿ™‚

2. Averill Farm outside Washington Depot ๐ŸŽƒ๐ŸŽ

Though I lived in Litchfield for years, it wasn’t until last year, after I moved away that I discovered Averill Farm. I found it perched atop Calhoun Street as I was driving the backroads of Washington Depot after a hike. (I suggest building in time to wander aimlessly and drive around Litchfield County to see what you can discover in these hills!) ๐Ÿš˜

Entering the long driveway into the farm, I couldn’t believe the sweeping view as the farm is perched atop a hill overlooking the Litchfield Hills. It’s an easy view to catch and you can also stock up on apple cider donuts, pumpkins, apples, eggs, and other local goods!

Truly a fall destination as it doesn’t open until mid-August, Averill Farm, a 10th-generation family farm, is a must-visit for fall in Litchfield County.

3. Spring Hill Vineyards in New Preston ๐Ÿท

Spring Hill Vineyards is another secret spot in Litchfield County and it’s just outside of Washington Depot. I bet you’ve driven right by the entrance on the busy Bee Brook Road which connects Litchfield to Washington Depot.

There is some sort of sign or archway that after driving this road for years, finally caught my eye and made me curious. I turned the car around and followed the long driveway up until a beautiful vineyard emerged.

view of spring hill vineyard with picnic tables and umbrellas and fire put and fall colored trees lining the property.

Dotted with picnic tables, food trucks, art sculptures, fire pits, and lawn games – it beckons you to slow down, have a seat, and take in the fall season. There are events with live music and even a small tower you can walk up and in and look out at the beautiful farm that dates all the way back to the 1700s. ๐Ÿ™‚ You’ll definitely get great fall pictures here!

4. Bunnell Farm in Litchfield ๐ŸŽ๐ŸŽƒ

I’m embarrassed to say that this is another spot I didn’t discover in Litchfield until after I left! Oh well. At least we know about it now. ๐Ÿ™‚

Bunnell Farm is a 5th-generation family-owned farm minutes from downtown Litchfield. When we arrived we saw two people getting everything ready and opening up the farm shop. I found out that they were brother and sister, so it’s truly family run!

They’ve got room for kids to run around, baby animals to visit, pumpkins and even two different barns offering all kinds of items. One barn housed lots of antiques and fall decorations and the other had produce, spices, and other things you would expect a farm to sell.

Absolutely a must-visit place for families as they have hay rides and even a corn maze that has flashlight maze nights! Sounds like a ton of fun and it’s right outside the bustle of downtown Litchfield. Bunnell Farm feels like a secret but now you can go find it! ๐Ÿ”ฆ๐Ÿ”ฆ

inside a big barn at bunnell farm in litchfield connecticut with tables set up with little antiques on the tables.
Antique sale inside barn at Bunnell Farm
red barn with fire pit in front and adirondack chairs arranged in a circle in front with a man sitting in one of the chairs.
inside bunnell farm with fall decor and racks of spices and fall knick knacks and decorations to buy.
Bunnell Farm store

5. Hollister House Garden in Washington ๐ŸŒบ

Built in 1770, Hollister House Garden is another hidden and historic gem in Litchfield County and a great one to explore in fall. Driving down quiet residential streets in Washington, you would never know the gardens that await you here.

Inspired by classic English gardens you’ll find winding paths, terraces, carefully designed plantings around every corner, and even a small waterfall in the midst of it all! If you want to wow someone, this is the place to bring them.

Early fall is a lovely time to visit as the gardens transition into autumn colors. While the roses have gone, dahlias take their place here in September. There are limited hours here and you must buy tickets to visit so be sure to check the website before you go!

garden path at hollister house gardens in washington connecticut with bright red japanese maple on the right of a stone pathway.

6. Topsmead State Forest in Litchfield ๐ŸŒณ๐Ÿ‚

This is a place near and dear to my heart! I came here almost daily when I lived in Litchfield and it’s where I brought my dog, Captain, all the time when he was a puppy. It’s quiet, peaceful, beautiful trails and scenes around every corner and absolutely perfect on a crisp fall day!

Topsmead State Forest feels like stepping back in time. The historic stone cottage sits in the middle of wide open fields surrounded by forest and stone falls. You’ll want to snap a photo around every corner. And don’t be surprised when you see photographers here for engagement photo shoots!

Itโ€™s a wonderful place for a quiet walk, especially in the fall when the trees around the property begin to change color and the gardens burst with autumn wonders! ๐ŸŒบ Open daily sun up to sun down.

fall garden at topsmead state forest mansion.
black dog on wide path lined with tall evergreen trees and orange colored maples.
Captain staring down a wide path at Topsmead ๐Ÿงก๐ŸŒฒ

7. Drive to top of Mohawk Mountain in Cornwall โ›ฐ๏ธ๐Ÿ

To get an easy foliage view without hiking, take the drive up Mohawk Mountain. From the top youโ€™ll find sweeping views of the hills and forests that define Litchfield County.

On a clear October day the landscape stretches endlessly in shades of red, orange, and gold. While it’s an easy view to catch I’ve never seen more than one or two other people here and several times we’ve been the only ones there which is always a treat!

8. Thorncrest Farm and Chocolates in Goshen ๐Ÿฎ

If you’re visiting the area of Litchfield in the fall AND you like chocolate – then I suggest driving down several scenic backroads, then a long dirt road, until you stumble upon Thorncrest Farm.

It is truly a gem in Litchfield County. Owners and farmers Clint and Kim treasure each and every cow they own. The milk to make the chocolates (and they sell the milk, too!) comes from cows on the farm, cows they name and treat exceptionally well.

I loved learning from Clint that he’s a vegetarian and unlike other dairy farms that often sell male cows off for veal – they raise the babies there and you can go visit them when born! They always post on their Instagram page when a new baby has arrived.

The cows are housed in the large barn where you can peak your head in and then the chocolates and treats in the smaller barn. It’s a unique farm visit that would be perfect to round out a fall day and drive home with some special chocolates! Get the dark chocolate sea salt truffle. ๐Ÿ˜

9. Visit Connecticut’s Tallest Waterfall in Kent ๐Ÿ’ฆ

multi-tiered waterfall in kent connecticut surrounded by green trees and a blue sky above.

Kent Falls is the tallest waterfall in Connecticut and it’s extra beautiful in the fall with the trees framing the water. I haven’t been here in peak fall yet, only late August when the leaves had just a yellow tint.

But I can only imagine the beauty with orange, yellow, green, and red leaves surrounding the multi-tier cascades tumbling down.

There’s a short and paved walk right from the parking lot making it an accessible spot for all to enjoy. You could get close to the bottom of the falls, snap a few pics, then turn back. Or you can take the short trail along the right side of the falls which comprises of staircases leading you to different viewpoints up along the waterfall.

10. Bantam Lake

Don’t miss a stop at Bantam Lake when exploring Litchfield County this fall. Connecticut’s largest natural lake is surrounded by colorful hillsides, making it a beautiful place for a scenic drive, a lakeside walk, or an afternoon paddle.

A fall lake reflection is mesmerizing and there are a few ways to catch it. There are a few ways to access and get up close to the lake. One way is parking at Point Folly. This is a campground that’s popular in the summer but we visited early last fall and most of the campers had gone. Park at the start and walk the road along the campground which takes you all along the lake.

Another way to access Bantam Lake, especially if you want to paddle or kayak, is from Sandy Beach. You do have to pay to park here but you don’t have to be a town resident which is the case for other beaches here.

Fall Day Trip Itineraries for Litchfield County:

If you’re thinking; this list is great, Kristen, but I’m new to the area and have no idea where these places are or how to link them together – then follow one of the itineraries below! I’ve got it mapped out for you with places that are a close drive together.

Litchfield County Fall Day 1: Best of Washington Depot

Litchfield County Fall Day 2: Best of Litchfield

  • 1st: Coffee and breakfast at Toast & Co. (the best and open early! ๐Ÿค๐Ÿ›)
  • 2nd: Hike/Walk at White Memorial (or choose a hike here: hikes in Litchfield, CT)
  • 3rd: Visit Bunnell Farm for pumpkins, animals, farm goods & corn maze fun!
  • 4th: Head to downtown Litchfield (West St) for lunch at: Petraroia Deli, West Street Grill or Marketplace Tavern
  • 5th: Stroll West Street for shops and North and South Street for historic homes & properties
  • 6th: Dinner at West Street Grill (upscale), Marketplace Tavern (casual), Arethusa (fancy! $$$), or La Catrina (mexican ๐ŸŒฏ)
  • ๐ŸฆBonus: Ice cream at Arethusa Farm in Bantam or Peaches n’ Cream in Litchfield

6 Top Trails in Litchfield County for Fall Views ๐Ÿฅพ

Fall is one of the best times of year to hike in Litchfield County. The air is crisp, the mosquitos are mostly gone, and the views across the hills are spectacular in red, orange, green, and gold! Below are some of my favorite hikes in Litchfield County:

1. Mount Tom Tower Trail, Litchfield

fall view from the top of Mount Tom Tower with ornage yellow and green trees in distance at sunset time with soft pink in sky.
view from top of tower

Mount Tom is a great hike for fall since you get to not only have great views for just 1.2 miles round trip but you get to hike to and up an historic stone tower! Though short, I would still be prepared with sturdy hiking boots. There’s a section that’s rocky and a little steep. But I’ve seen kids of all ages hiking here, it’s a ton of fun!

2. Waramaug’s Rock via Meeker Trail, New Preston

This is one of my favorite hikes in the state. First, it’s one of the most beautiful areas in Litchfield County so I never mind the drive. I love the little boardwalk that starts the hike and takes you into Macricostas Preserve which is just jaw dropped in itself. You can enjoy a very beautiful walk in here for a half mile before heading into the woods and starting the elevation to the view. I love just this part through the meadow but of course the hike up to the view is completely worth it especially in the fall!

3. Hidden Valley Preserve in Washington Depot

If you prefer a mainly flat and easy trail with pretty fall scenery then Hidden Valley Preserve is a good one for you! There is a longer loop that’s 3.5 miles, but you can get to the Van Sinderen Suspension Bridge over the Shepaug River after just a tenth of a mile. If you want even more choices check out my post โžก๏ธ 10 Hikes Near Washington Depot โญ๏ธ

4. Beaver Pond Loop at White Memorial Conservation Center, Litchfield

With over 4,000 acres of protected land, White Memorial Conservation Center is one of the best places for walking in Litchfield. The trails wind through forests, fields, wetlands, and open meadows. While there are sooo many trails to choose from in White Memorial – the one I included above is one of my favorites with the loop around Beaver Pond and Plunge Pool. The reflection of the fall leaves in the water make it a standout hike in the fall!

5. Appalachian Trail in Falls Village

rolling mountains in distance with orange maple trees dotting the landscape in foreground in litchfield county in fall.
Rand’s View ๐Ÿ’š

The Appalachian Trail runs from Georgia to Maine and we are lucky to have about 51 miles of the Appalachian Trail in Connecticut! And it runs through, of course, the northwest corner AKA Litchfield County. There are so many hikes to choose from along the AT but I included one of my favorite views above – Rands View. With the rolling green mountains int he distance and the orange maple trees dotting the landscape and framing the photo – it’s breathtaking in the fall. I hope you like it, too!

6. Pine Knob Loop in Sharon/Cornwall

pine knob loop hike connecticut
Lookout at sunrise..
pine knob loop hike connecticut

I know I keep saying this – but we’ve got another one of my favorite hikes on the list here! I think it’s just because Litchfield County is truly, in my opinion, one of the most beautiful areas (and most hilly!) in the state. So you’ve got a lot of opportunities for big views here. Pine Knob Loop is another outstanding trail to get elevated and spy all the fall foliage mixed in with the rolling hills of the Housatonic River Valley below. As you hike up you’ll walk along Hatch Brook Falls – so there’s lot of good water for the dogs, too!

Litchfield County Towns in the Fall ๐Ÿš—๐Ÿ

Get inspiration for your fall visit with photos of a few stand-out towns in Litchfield County below!

Fall in Litchfield

Litchfield is a classic New England town that’s a must-visit. The historic town green, white church steeples, and tree-lined streets are surrounded by hills that burst into color.

Take a walk along North Street or South Street, grab a coffee at one of the numerous cafes in town, and enjoy wandering through one of Connecticutโ€™s most beautiful small towns! Be on the lookout for Litchfield Historical Society’s ‘Scarecrows in the Meadow’ fall event at Tapping Reeve School on South Street.

Fall in Kent

Kent is another most popular fall town in Litchfield County, and for good reason. Surrounded by the hills of the Appalachian Trail, protected forests, and winding country roads, itโ€™s a super scenic place to explore once the foliage peaks.

My perfect day in Kent involves a hike on the Appalachian Trail (I suggest Hoyt Rd to Bull’s Bridge) walking the downtown and popping into the small shops, Wilson’s for lunch or Kingsley Tavern for dinner! Kent is also home to one of Connecticutโ€™s most famous waterfalls, Kent Falls.

Fall in Washington and Washington Depot

Washington, or commonly known as Washington Depot) is a peaceful countryside town filled with farms, scenic preserves, and beautiful landscapes. In the fall the hills surrounding the town glow with color and it feels like a ‘wow’ moment every bend in the road.

My perfect day in Washington Depot involves, of course, a hike near Washington Depot, then exploring the downtown and lunch at a cafe. For a classic New England dinner and restaurant try the historic GW Tavern perfect for fall with its rustic interior and big stone fireplace!

Fall in Cornwall

Cornwall feels tucked deep into the hills of northwest Connecticut and is one of the most scenic towns in the county. Quiet backroads, the red covered bridge, and the Housatonic River make it an especially beautiful area in fall!

My perfect day spent in Cornwall involves a hike (suggest the Housatonic River walk!), a croissant, smash burger or fried chicken sandwich from Cornwall Market, then a drive to the West Cornwall Covered Bridge!

Fall in Salisbury

Salisbury is about as far in the northwest corner of CT as you can get! It’s got a bliknk-and-you-miss-it downtown but it’s still very scenic and worth the drive, especially with all the big hikes around.

My perfect day in Salisbury involves a hike (try Bear Mountain, CT’s tallest!), pastry and coffee from Sweet Williams or a sandwich from LaBonne’s Market, and a stroll downtown in and out of the cute shops!

Scenic Fall Drives in Litchfield County

Just by visiting the fall spots on this list you’ll be driving down some pretty incredible backroads. But if you want more specific drives to plan into your route check out the following:

Drive Around Lake Waramaug

The drive around Lake Waramaug is one of the most beautiful in CT. The road winds along the shoreline with sweeping views of the lake in between some just as impressive to look at lake houses! Go slow and take it in.

Laurel Ridge Road in Litchfield

Laurel Ridge Road is one of my favorite roads in Litchfield. The road runs along Laurel Ridge Farm with nothing but cows dotting the open landscape as you pass by. This is also an amazing spot to pull over and watch the sunset! (shhh, secret from a local!) ๐Ÿ˜‰

Backroads Around Cornwall

The countryside around Cornwall is filled with quiet scenic roads, historic farms, and forested hills. During peak foliage season, this area is especially peaceful and picturesque.

And When is Peak Fall Foliage in Litchfield County?

Peak fall foliage in Connecticut usually arrives in mid-October and same for Litchfield County. Though it is further north in CT, peak foliage typically occurs earlier than in other parts of the state.

Early October usually brings the yellows, while mid to late October when we see the most vibrant shades of red, orange, and gold. Fun!

Final Thoughts…

I hope you loved this guide all about Litchfield County in the fall. It’s one of my favorite areas for day trips in CT, no matter the season.

And since I used to live in Litchfield and live close enough now, I really feel like I’ve explored it well and have a lot to share with you.

Although – one of my favorite things about this area is that it continues to surprise you. I still find new spots – backroads, pretty views, farms, and places I never knew existed…

So keep getting out there and exploring. Use this post as a guide but my number one suggestion would be to turn down that road that catches your eye, take the time to slow down, turn around, and pull over (safely)!

Happy fall exploring! ๐Ÿโค๏ธ๐Ÿงก

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