Fall in Connecticut is the best! Actually… fall pretty much anywhere is the best.

But I first visited Connecticut in 2019, on a quick stop at the Gilmore Girls towns, and I can’t stop coming back (and always in the fall!). It’s less crowded than other popular New England locations, but is still dripping with autumn charm.

Connecticut has the oldest cider mill in America, a castle filled with secret passageways that’s surrounded by fall foliage, a historic (Hogwartsy!) college known for their Halloween show, and So. Much. More.

So get excited, because we’re about to embark on the absolute BEST 1-week fall in Connecticut road trip!

Years Visited: 2019, 2021, 2023

Time of Year: October

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What’s in this Article:

• Best Time of Year to Visit
• Day 1: Arrive in Hartford
• Day 2: Explore Hartford
• Day 3: Gillette Castle & Essex
• Day 4: Mystic
• Day 5: New Haven & Yale
• Day 6: Fall Foliage Train Ride
• Day 7: Return Home

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Best Time of Year for Fall in Connecticut

Fall in Connecticut ranges from about mid-September to mid-November.

The best time to come for fall foliage is the end of October. Accommodation prices also tend to be a lot cheaper the last week of October than earlier in the season.

Most seasonal activities (like cider mills) will be open the entire fall. However, make sure you pay attention to opening dates. For instance, if you want to tour inside Gillette Castle, you will have to visit on a weekend on or before Columbus Day.

Also check for festival dates and fall events that you might want to plan your trip around. Usually in mid-late October the streets of almost every Connecticut town are decked out with scarecrow contests! There is also the famous Yale Halloween Show on Halloween night.

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Fall in Connecticut Day 1: Arrive in Hartford

This road trip will begin and end in Hartford, the capital of Connecticut.

If you’re flying, you can fly into Bradley International Airport in Hartford and pick up a rental car. If you live close enough to drive, then just begin your road trip at whichever stop is best for you.

Map of Road Trip Route:

Arrive in Hartford, CT

There won’t be too much planned for today, as it’s mostly a travel day. Once you arrive in Hartford, here are a couple of suggestions of easy things to do for the rest of the day.

Things to Do in Hartford:

• Wander the award winning Elizabeth Park.
• Take a cruise on the river.
• Tour the Capitol building and Bushnell Park.
• Visit the Wadsworth Atheneum Museum of Art.
• See a show at The Bushnell theater.
• Do one of the local fall activities!

Fall Activities in Hartford, CT:

• See fall foliage on a hike near Hartford.
• Foliage and lantern tours of Ceder Hill Cemetery.
• Corn maze, hayrides, animals and pumpkin picking at Foster Family Farm.
• Corn maze, pies, or the annual Autumn Fest at Lyman Orchards.
• Attend Nightfall in Elizabeth Park.

Where to Stay in Hartford

There are a lot of options for places to stay in Hartford. You could get a hotel downtown, or stay at a cozy B&B in Old Wethersfield. But I think the best places to stay would be a VRBO or Airbnb rental with a fire pit or hot tub, if you can find a good one. When I visited, I stayed at a perfect little cottage with a fire pit and a garden that I 100% recommend.

Here are a few suggestions to get you started:

• The Chester Bulkley House
• Silas Robbins Bed & Breakfast
• The Capitol Hotel
• Windy Top Cottage

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Fall in Connecticut Day 2: Explore Hartford

Morning: The Mark Twain House

One of the best things to do in Hartford is to visit the Mark Twain House. It’s an eccentric mansion surrounded by fall foliage in the heart of the city.

I highly suggest booking a costumed actor tour, which was so much fun. Different characters lead different tours, so you could even book this more than once and learn new fun facts about Samuel Clemens… er… Mark Twain.

Don’t forget to visit the bookstore and museum at the visitor center. You can also tour the Harriet Beecher Stowe Center, which is right next door to Mark Twain’s house!

• Psst: If you like travel and reading, check out my list of the best travel books to read, including one I picked up at the Mark Twain House!

Afternoon: Old Wethersfield & Fall Activity

After your visit to the Mark Twain House, head over to the cute village of Old Wethersfield, in the Hartford suburbs. This little village looks just like Stars Hollow, and is the perfect place to grab some lunch and wander the streets for a while.

There are lots of options for lunch on Main Street, plus shops and historical museums. There’s also a large town green and a local farm stand you can visit.

• Good to Know: A lot of the little shops in Old Wethersfield are closed on Mondays and Tuesdays. Most restaurants are open all week.

After exploring Old Wethersfield, you can spend the rest of the afternoon doing one of the Hartford fall activities listed above. Try the hay rides and corn maze at Foster Family Farm, or maybe head out on a short hike through the woods.

Evening:

Spend the evening relaxing and enjoying the fall vibes of Connecticut. Depending on when you visit, you could do a spooky lantern tour in the cemetery, go to a Halloween show (or just a regular show, that’s cool too) at The Bushnell theater, or just relax by the fire at your Airbnb.

You can grab dinner at one of the international restaurants on Farmington Ave. (just down the street from the Mark Twain House), or try out another local restaurant in Hartford.

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Fall in Connecticut Day 3: Gillette Castle & Essex

Morning: Gillette Castle State Park

Gillette Castle State Park is about a 45 min. drive from downtown Hartford. It is one of the best places to see fall foliage in Connecticut!

Gillette Castle was the retirement home of Sherlock Holmes actor William Gillette. He designed and built the house on top of a cliff overlooking the Connecticut River. The inside is filled with secret passageways and fun artifacts.

There are also lots of fun trails to walk through in the woods around the park.

Things to know about visiting the castle:

• The state park is open year round from 8 am – sunset. The visitor center bathrooms are also open year-round.
• However, restaurants and castle tours are only open from Memorial Day-Columbus Day.
• Fall tours inside the castle are only available on weekends from Labor Day-Columbus Day.
• The road up to the castle is very steep and windy (but beautiful!).
• The best time for fall foliage is the end of October. I was there the last week of Oct, and the leaves were stunning!

Afternoon: Explore Essex

After exploring Gillette Castle, head 1/2 an hour to the historic village of Essex. This popular spot is full of boutique shops, historic museums, Christmas movie filming locations, and a gazebo overlooking the water. Not to mention The Griswold Inn, which is one of the oldest inns in America (opened in 1776!). Oh, and truffle shots.

Get lunch (or dinner, depending on how your day’s going) in downtown Essex and take some time to explore all the shops and things to do.

Then drive another 1/2 hour to Mystic for the next two nights.

Where to Stay in Mystic

Prices in Mystic tend to be very high earlier in the season. I visited the last week of October, and the prices were great! But when I looked at booking the same hotel for a September trip, I was shocked at the price!!

There are still reasonably priced places to be found earlier in the season, but you will probably have to stay a little further out of town. So just be sure to check the prices for your dates, and don’t be afraid to stay in somewhere nearby instead of right in Mystic.

Here are some options of where to stay:

• Hampton Inn & Suites
• Spark by Hilton
• The Whaler’s Inn

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Fall in Connecticut Day 4: Mystic

Morning: Mystic Seaport Museum

First get breakfast (or if your hotel offers breakfast, then get second breakfast!) either at Deviant Donuts or Sift Bake Shop.

Spend the morning exploring the huge Mystic Seaport Museum!

• Good to Know: The museum is open daily from 10-5 in September and October, but there are extra attractions open on the weekends in the fall. The museum closes at 4 pm, starting November 1.

Afternoon: Mystic Aquarium or Boat Ride

There are a lot of fun things to do in Mystic, so there are so many options for things you could fill your afternoon with. The Mystic Aquarium is one of the most popular things to do, but you could also take a boat ride (or kayak) out on the water, relax on the beach, wander around the shops downtown or Olde Mystick Village, get ice cream, or just relax at your hotel (maybe they have a pool or hot tub!).

Evening: Downtown Mystic

In the evening, you have to try Mystic Pizza! You can walk in and order just a slice, place a pick up order online, or sit down in the restaurant. I really liked their pizza!

There are also a lot of restaurants you could check out in Olde Mystick Village. Or have one for lunch, and another for dinner!

Spend the rest of the evening wandering the shops downtown or in Olde Mystick Village. There is also a movie theater in the village.

*Day 4 Alternative:

There is a fall foliage train ride on Day 6 of this Connecticut road trip itinerary. However, that train only runs on weekends. If that doesn’t work out with your schedule, or if you’d just rather ride the Essex Steam Train, you can do that today, instead of exploring Mystic.

If you choose this alternative, then I would head straight to Mystic after Gillette Castle the previous day, as you could then explore Essex before/after the train ride today.

You can also add a boat ride on the Connecticut River (with views of Gillette Castle!) onto your steam train ride.

If you have the time, spend a day in Mystic, and another day doing the Essex Steam Train!

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Fall in Connecticut Day 5: Yale & New Haven

Morning: B.F. Clyde’s Cider Mill

First stop of the day is the oldest continually operating cider mill in the country: B.F. Clyde’s Cider Mill! Grab a cider and donuts, or a slice of their famous apple pie (for breakfast, or for a snack later).

• Depending on where your hotel is located, the cider mill will probably be a few minutes out of the way for the trip to New Haven, but it won’t add too much time. However, you could visit the cider mill on a previous day, if you would rather head straight from Mystic to New Haven.

Afternoon: Tour Yale University

New Haven is a 1 hr. drive from Mystic. You can park at your hotel and walk to all the downtown attractions, or if that’s not an option, the best place to park is the Shops at Yale parking lot.

Public tours of campus are free, and take place at 1 pm, Monday-Saturday. Just be sure to book your tour online ahead of time.

The tour will take you onto parts of campus that are not open to the public, and will also point out the popular sites to visit, but will not go inside any of them. Spend the rest of your time at Yale exploring these popular spots:

• Beinecke Rare Book & Manuscript Library
• Sterling Memorial Library
• Peabody Natural History Museum
• Yale University Art Gallery
• Yale Center for British Art

Evening: Dinner and a Show

There are so many good places to eat dinner in New Haven! You can get Indian from Sherkaan Indian Street Food, tacos from the Long Wharf Food Trucks, pizza from Frank Pepe’s, or the original hamburger from Louis’ Lunch!

After dinner, why not see what performances are happening around New Haven? There are so many options for students performances, like theater or music, in addition to plenty of other theaters in the city.

Or, if you’re here on Halloween, you can attend the famous Yale Symphony Orchestra Halloween Show! Just be sure to book your tickets ahead of time, as they do sell out.

• Good to Know: Apparently tickets to the 2024 Halloween Show sold out in 5 minutes! So you probably don’t want to plan your trip around it…

Where to Stay in New Haven

It’s great to stay at one of the fancyish hotels right in downtown, so you can just walk around everywhere. They are a bit expensive, so I opted for an Airbnb apartment that was just a 15 minute walk to downtown (with free, off-street parking). But you can always park downtown, if you end up staying somewhere outside of the main city area.

• The Study at Yale
• Graduate New Haven
• New Haven Hotel
• Omni New Haven
• New Haven Village Suites

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Fall in Connecticut Day 6: Foliage Train Ride

Morning: Fall Foliage Train Ride

45 minutes from New Haven is the Railroad Museum of New England. You can embrace your inner Sheldon and nerd out over all the old rail cars they have on display.

But the the real reason we’re stopping here is to do a fall foliage train ride! As a bonus, the train even stops at a chocolate shop on the way!

• Good to Know: Autumn Colors train rides only take place on Saturdays and Sundays. If this doesn’t fit into your schedule, you could ride on the Essex Steam Train earlier in the trip.

Afternoon: Hogan’s Cider Mill

Hogan’s Cider Mill is just 15 minutes from here, and is one of the best things to do for fall in Connecticut!

This famous stop has apple cider, hard cider, famous donuts, mini golf, and lots of great fall photo opportunities! Hogan’s Cider Mill is open Thursdays-Sundays. I was so bummed that they were closed the day I was passing through, so make sure you plan your trip to allow a stop at this Connecticut staple!

Then drive about 30-40 minutes back to Hartford for the evening.

Evening: Back in Hartford

With one final night in Hartford, you have more time for a corn maze or haunted tour in Hartford. You can stay at the same hotel where you stayed at the beginning of the trip, or try somewhere new (since it’s only one night, you could splurge on a nice spot for tonight!).

Or, to save money and vacation days, you could just head straight back to the airport this morning (it’s only a one hour drive from New Haven, so you should have plenty of time to make it for an afternoon flight home).

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Fall in Connecticut Day 7: Return Home

Now that we’re back in Hartford, it is time to fly (or drive) home.

But if you have more time, consider adding a trip to Vermont, or perhaps Cape Cod, Plymouth, and Boston (perfect in fall!).

• Good to Know: Vermont fall colors change sooner than Connecticut, so you would want to go there first, and Connecticut second.

You can also check out these guides for more ideas:

• The Best Things to do in Connecticut
• Gilmore Girls towns in Connecticut
• Guide to Visit Yale & New Haven
• 1-Week Gilmore Girls New England Road Trip
• Fall Travel Guides

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There are so many great things to do for fall in Connecticut! I tried to pick out the absolute best things to do, based on all of my research and three (hopefully four soon!) Connecticut road trips.

Any more questions?

If you have any questions about planning to visit Connecticut in the fall, feel free to email me or comment below. Or if you have more ideas of things to do, please share them!

Planning to visit Connecticut?

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You might also like:

• The Best Things to Do in Connecticut
• Guide to Yale and New Haven
• Gilmore Girls Towns in Connecticut
• Things No One Tells You About Stowe, VT
• The Complete Guide to Visit Cape Cod
• 12 Real Life Towns like Stars Hollow

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