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Fall Things To Do In Connecticut #FALLINCT

Connecticut may have four seasons, but in my opinion, fall is undoubtedly the best. There is just something about the crisp air, colorful changing leaves, and all the fall activities that make my heart feel so full. Oh and I am an October baby (and so is my hubby), so I was destined to be biased regardless.

PS, if you're new here my name is Stephanie and I am a wanderlustin, fashion obsessed, spicy margarita enthusiast. Follow me along on instagram @sugaredstilettos to see all that and a big dose of my daily life… I love new friends!

I look forward to the fall season every year because I get SO excited thinking about all the fall things— pumpkin patches, apple picking, hayrides, leaf peeping, fall cocktails, and SPOOKY SEASON! Connecticut is jam packed with hidden gems and things to do, so I thought I would take the guess work out of it for you and put them all in one place.

SO get your flannels and booties on because you have things to see before fall ends!

I made a key so it's easier to tell what each recommended spot below has!

🎃= pumpkin patch

🍎= apple picking

☠️= scary

🌾= hayride

🌽= corn maze

🍻 = has alcohol (cider, pumpkin beer, etc)

🎡= amusement rides

🍴= has food

HOGANS CIDER MILL (Burlington, CT) 🍻🍴

Putting this one at the top of the list because I wish I personally could have discovered this place sooner than I did, it's AMAZING. Home to the Hogan's Drunken Donut which is Hogan's fresh pressed cider, spiked with their December frost cider and topped with a cider donut, whipped cream, and sprinkles—— literally delicious. They also serve their cider by the glass or in flights of 4. Their ciders are pressed from locally grown apples and they don't taste like they are loaded with sugar like most ciders do.

They have quite a few tables and chairs available, but I personally recommend bringing a blanket, a board game, and setting up a spot somewhere to enjoy your cider and stay awhile!


Home to a mini pumpkin patch, a corn maze, an apple orchard, and a large store that houses their apples and local baked goods/products. If you go on the weekends expect there to be a bit of a line to get into the store, but just know it does move quickly! This place is literally a one stop shop and it's very kid friendly. Each year they have a different corn maze theme so you can keep coming back for a new challenge— this years theme is Rock 'n Roll of the 1970s. The maze takes approximately 30-40 minutes to complete and is $10 for adults and $6 for kids (free under age 3).

PS… Their apples are some of my favorites, so if you're looking to go apple picking and want a photo worthy apple orchard I highly recommend it!


Full disclosure I haven't done any of these because I am a baby, BUT if you are somebody who loves getting scared then these are some of the top rated options all over CT.


Unfortunately, this one has already come and gone, but I am including it so you can mark your calendars for next year because it's a great little town festival! It's a 6 day event that takes place over the first two weekends (Friday-Sunday) of October.

If you're a foodie come check it out because they have some drool worthy options to munch on. One of which is the apple fritters, THEY ARE OUT OF THIS WORLD. Some people come to this festival for the sole purpose of getting these fritters. They literally have giant chunks of apples inside them and are made fresh by the minute because the line wraps down the block of people waiting to get their hands on them. There is also a mini carnival with amusement rides, live music, and TONS of local vendors selling their products.


This family owned and operated farm is so dang cute and picturesque... it's actually one of CT's 10 oldest continually running farms! It is home to beautiful mums, hayrides, a pumpkin patch, apple fritter/cider + fried dough/oreo food trucks, and a small store selling local goods and the farm's produce. Unfortunately, this year the hayrides to the pumpkin field are not operational due to the rain making the fields un-driveable, BUT there are still tons of great pumpkins plump for the picking!

There is also the cutest photo op here in front of the "Pickin Patch" sign!


Lake Compounce is a family amusement park that has been around for 175 seasons! It's also where Happy Hauntings takes place every Saturday + Sunday in the month of October from 10am-6pm. Happy Hauntings is a brand new family friendly halloween experience that has it all! There is a pumpkin patch, a hayride, a slime factory, two corn mazes, and tons of fall themed food options!


Looking for a great dinner spot that hits the seasonal cocktail spot? This restaurant is constantly adding fun + funky options to their menu… hence the name Uncommon Grill. They are also known for having awesome seasonal cocktails, so if you're in the mood for a unique fall drink and a great dinner I highly recommend this place. I mean look at this cocktail list!!


PS. while you are in Watertown be sure to swing by Horatio's Bar. It's owned by my hubby and is a local neighborhood bar that is decked to the nines in Halloween decorations around this time of year, so it makes a great spot for after dinner drinks with friends!


Fall fest is in full swing over at Silverman's farm for the month of October! This farm has the most beautiful fall foliage back drop with colorful displays of squashes, gourds, haystacks, and cornstalks— aka a great place for fall photo opportunities! This farm has a pumpkin patch and gives you a chance to win a free pumpkin! Before every purchase, you get a chance to guess the weight of the pumpkin you picked and if you are within 2oz your pumpkin is free! They also have scenic tractor rides on the weekends from 9AM-430PM and an animal farm and market that is open daily from 9-5pm.

Photo: @silvermansfarm


I'm headed to Mystic for my 30th and this is on my list of spots to stop at. Follow me along on IG (@sugaredstilettos), so you don't miss my stories!

Anywho, this family owned and operated farm has been around since 1881 and is the oldest steam-powered cider mill in the US! They are open from 9-6pm in September and October and from 9-5pm in November and December. They have an on-site bakery that whips up cider donuts, jelly donuts, apple turnovers + dumplings, and so much more. They also have seasonal wines and hard ciders and offer tastings on the weekends. I personally have my eyes on the Spider Cider which is infused with pumpkin spices, I'll let you know what I think of it!

Photo: @clydescidermill


I got invited to a PR event this week at RHK so follow my IG stories (@sugaredstilettos) to see what it's all about because I will obviously be taking tons of pictures!

From October 11-31st RHK has an extensive artisanal fall cocktail menu; here are some of the options!

  • Urusula's Bloody Mary This pseudo scary bloody Mary, inspired by Ursula, the witch in Disney’s Little Mermaid movie, is close to black in color and big on taste. The Ursula is only available from October 25* – October 31.

  • Pumpkin Mule

  • Good Harvest

  • Pumpkin Fluff

RHK is also known for their drool worthy burgers and milkshakes, so if you're in the area and want some food and drinks worthy of the Gram then come check it out!


This one is on my list to go see! They have homemade donuts, seasonal cocktails, apple picking, a corn maze, pumpkin patch, and tractor rides! So, yes it has everything you would find at a traditional farm, but with a wine and cider barn.

Photo: @holmbergorchards


Another one on my list to try is the Essex rail-bike trail that takes between 90-120 minutes to complete. You can choose between an 8 mile (moderate) or 9 mile (difficult) trail. The trails take you from Essex Station, along the CT river to Chester, CT and back. It's a great way to soak in some scenery and get a good exercise in! The 8 mile trail runs Friday through Sunday from September 11 to October 31st and the 9 mile trail runs Friday through Sunday from September 11th to October 24th. FYI riders must be at least 8 years old!


This winery is surrounded by acres of beautiful scenery making it a beautiful spot to come unwind with a glass of wine.... or even better one of their seasonal wine slushies. This month's was Spiced Pumpkin with whipped cream! I actually had my bridal shower here in their upstairs room (full blog post here), so if you need a spot for a private event definitely check it out!

Photo: @hawkridgewinery

PS they are also are having a faux pumpkin paint & sip on October 20th from 6-8pm (click here to sign up)!


Did you know that October is the best time to go leaf peeping in CT because the leaves are at their brightest?

If you are the adventurous type and want to see some fall foliage by foot here are a few awesome hiking options.

1. Talcott Mountain State Park (Simsbury, CT) — A 1.25 mile hike to the top where the 165ft Heublein Tower and sweeping views of fall foliage await.

2. Lover's Leap (New Milford, CT) — A short 0.4 mile hike that crosses over a stunning iron bridge.

3. Chauncey Peak (Meriden, CT) — Approximately 1 mile hike that gives gorgeous views of fall foliage off the lake it overlooks.

If you would rather see the fall foliage by car and are looking for a scenic route to take then check out Visit Connecticut's write up called "CT Fall Foliage Drives in 2021" that literally maps out tons of different routes and dining options along the way!

If you think I missed something worth checking out let me know because I still have three weeks left of fall activities to do!

Love Always,

Sugared Stilettos

(By Stephanie


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