Growing up in Florida means you don’t really get the opportunity to experience the changing of seasons! Here in Miami, it’s pretty much always summer and extremely humid. I have always dreamed of experiencing the vibrant fall colors in New England, with the ultimate road trip through Connecticut and Vermont. New England is renowned for its breathtaking fall colors, with vibrant red, orange, and yellow hues of the region’s trees.
When I saw the activities to do in New England during the fall, I thought it sounded like the perfect trip to do with a toddler. Apple picking, hay rides, farms, sweet treats? What’s not to like, right? Of course, everything with a toddler does take a special set of skills to plan the right trip to limit meltdowns, build in some nap time, and maximize your vacation time as well. If you’re planning a family trip to see the fall foliage, this blog post provides details for my exact trip including where I stayed, ate, useful tips and stunning visuals.
When to Visit New England for Fall Foliage?
First, I recommend you check the leaf peeping tracker. This is crucial in order to plan your trip to see the leaves at their peak. There are so many factors that affect the color: rain, wind, temperature, etc. To ensure you get the most out of your New England fall foliage adventure, it’s important to pay attention to the weather and be flexible. Peak fall foliage in New England starts in the north and works its way down south. So if you’re earlier in the season, the farther north you’ll start, or later in the season, you’ll go further south. Meaning leaves start to change first in Maine, New Hampshire, and Vermont, then in Rhode Island, Massachusetts, New York, and Connecticut. Your best bet overall for stunning fall foliage on your road trip is to visit late September through mid October.
We visited during the second week of October and spent 4 days exploring, but if you can stay at least one week, I would definitely do it! There is so much to see and do and driving from place to place can cut into a decent portion of your vacation time.
How to get around New England?
Renting a car is an absolute must for the ultimate New England Road trip! Make sure to secure a vehicle early as Fall is extremely busy in this part of the country. Like you, many others choose to take East Coast fall road trips in the hope of seeing the incredible beauty that comes with the changing of seasons. This means car rental companies hotels and vacation rentals can book out well in advance, leaving the remaining last minute bookings quite expensive.
My Itinerary
Day 1: Miami –>Hartford –> Woodstock
We decided to fly from Miami International Airport to Hartford, Connecticut, which is approximately a 3 hour flight. We picked up our rental car at the Avis location within the airport and started making our 2.5 hour drive to Woodstock, Vermont. We preferred to make the drive to Woodstock after flying into Hartford so we could begin a full day in Vermont on Day 2. We checked into our Marriott Hotel in Hanover Lebanon and settled in before heading to dinner at Worthy Kitchen.
Day 2: Woodstock
Woodstock is known as the “prettiest small town in America.” A gorgeous and charming town with great restaurants and a stunning resort. We decided to spend the day exploring this adorable towns main spots like The Woodstock Inn, Central and Pleasant Streets and Middle Covered Bridge.
During our day in Woodstock, we had breakfast at Soulfully Good Cafe, lunch at Mon Vert Cafe, and ice cream at Woodstock Scoops.
Day 3: Woodstock –> Hartford –> Wethersfield –> Wallingford
On our third day, we decided to head back to Hartford to explore the foliage in Connecticut. We began our 2.5 hour drive early in the morning so that we could make the most of our day. First, we dropped off our belongings at our Marriott hotel in Rocky Hill. After our drive, we were hungry and headed to grab lunch at The Charles, which is located in the cutest town called Wethersfield, CT (15 min drive from our hotel). After lunch, we walked the town of Wethersfield, stumbled upon an Heirloom Festival and explored all the shops on Main Street, even scooping up ice cream at Main Street Creamery and Cafe.
The baby was ready for a nap by this time, so we hopped in our car and decided to visit a local vineyard in Wallingford, CT called Gouveia Vineyards. The vineyard was only a 30 minute drive and the perfect spot to unwind and relax at the end of our day. We watched the sunset over 32 acres of woodlands and pristine vineyards. You can bring your own pizza, snacks or food to pair with your wine at this particular vineyard.
If you have more time in Connecticut than we did, here is a list of other vineyards within a 45 minute drive of the area:
Day 4: Hartford –> New Haven –> Guilford
Our 4th day involved spending the first part of our day in the town of Guilford, CT (45 minute drive) to visit Bishop’s Apple Orchard Farm, Market & Winery. If you’re traveling with kids this is great place to visit as they hold a Fall Festival starting in September. During this time, Bishop’s Orchards offers apple picking, wagon rides, corn maze, bounce house, slides, rides, pumpkin patch and more.
After spending several hours at the Orchard, we then decided to drive to New Haven, which was on our way back towards our hotel, for lunch at Frank Pepe’s on Wooster Street. Everyone spoke highly about Frank Pepe’s pizza in Connecticut, so we had to try it for ourselves! It was a very casual spot with great pizza, which I recommend if you’re in the New Haven area. They also have locations all throughout Connecticut, so you can look up the closest restaurant to you.
Following lunch, we decided to stroll some of the New Haven area before heading back to Hartford to our Hotel to rest for the night.
Day 5: Hartford –> Miami
Our fifth day consisted of traveling back home. We opted for an earlier flight and headed to the Hartford airport (30 minute drive) to drop off our rental car and catch our flight to Miami!
I hope this helps you plan an incredible New England fall road trip! I really enjoyed this trip with our daughter so much and would encourage you to visit too! The memories will be with us forever. We are hoping to visit next year and explore different towns to catch even more of the beautiful leaves changing colors.
Have you been leaf peeping in New England? Where are your favorite spots?
SHOP MY FALL LOOKS
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