Writing this in hopes that all of you guys can do this New England Fall foliage road trip yourself one day! It was a trip of a lifetime, but I definitely would have done a few things different. Luckily, I did all of the not-so-great things first so now you guys don’t have to!
Before starting this fall foliage guide, you should know that it was HARD with a baby. Miller was 11 months old and even though she is such an amazing baby, the traveling took a toll on her. In fact, she got strep towards the end of the trip. I would definitely wait until your child is older to do this trip with them. It will be more enjoyable for everyone.
That being said, it is a trip you MUST take within your lifetime. I am going to share what we did because we had an 11-month-old with us and what we would have done if she wasn’t with us so that you can have two sides to this road trip (in case you want to bring your own child!)
The dates we went: Oct 8-16th. The leaves were at their prime for our entire trip.
New England Fall Foliage Road Trip
We went by the Loney Planet Fall Foliage guide. You can buy it HERE. They also give a free overview of the guide HERE with the map. We did a lot on this map and we added some of our own things, so you can definitely go off both when planning your own!
Here is the map we used,
and then we added on a little at the end. What the guide doesn’t tell you is 1. where to fly in 2. a drive to get back to where you started 3. where to eat 4. where to sleep!
We flew in to LaGuardia Airport in New York City to start this New England Fall foliage road trip. It was the least expensive option for all of the airports close to Danbury, CT (where the road trip starts.) It was also the only non-stop option at the time of booking.
LGA airport was about an hour and a half from Danbury. We drove in and immediately went to the grocery store to pick up things we needed for the trip. We bought a few things for Miller, water, snacks, and some easy things we could eat for breakfast/lunch that didn’t need to be refrigerated.
After the grocery store we stopped here (below) at Squantz Pond State Park. It was beautiful. We got Miller out of the car and pushed her around in the stroller a bit. This was the first peek of some gorgeous fall foliage.
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We were going to go to American Pie, a diner close by, for dinner, but some locals told us to go to The Hopkins Inn. We are SO GLAD we did! It is a super charming hotel that had three fireplaces running. Nothing is better than the smell of firewood. They served German food and we loved everything we ordered. Try to get there before sundown to see a beautiful sunset on the lake.
We stayed at THIS Airbnb in Kent and loved it.
Things we wanted to do but didn’t get to: Gone Ballooning. We wanted to do a hot air balloon ride over the lake but couldn’t with a baby. We also wanted to go to DiGrazia Winery but they were closed on Tuesday. If you have the time, add these to your list!
Day 2 was super rainy all day. We made it to Cobble Mountain for a hike and finished it right before the rain started coming down. Just look up Cobble Mountain in the All Trails App for the address. The hike was beautiful and definitely worth it! It is a definite MUST DO on this New England Fall foliage road trip!
Due the rain we spent most of the rest of the day in the car. We drove through Kent and saw Kent Falls, then drove through Housatonic River State Park and saw the Cornwall Bridge. The drive was stunning, even in the rain. We checked in to Lantern House Motel (wouldn’t recommend it, but we got the room last minute so we didn’t have tons of options) in Great Barrington. We shopped a little around town and then had dinner at a brewery there called Barrington Brewery & Restaurant and we loved it! We sat in the bar area and talked to locals all night.
We stayed at the Lantern House Motel and would not recommend it!
In the morning we hiked Beartown State Forest. It is a tough incline and nothing really to see at the top but it was a pretty walk. If you look up this address on All Trails, make sure you go to the trailhead at the opposite side of the street from where you park. We got lost and walked two miles extra because of it!
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After the hike we drove up Mt Greylock, which is a New England Fall foliage road trip MUST!! The drive up the mountain took about 20 minutes but it will take your breath away! Make sure to climb War Veterans Memorial Tower while you are at the summit.
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We stopped at two breweries on the way to our hotel. I would skip Bright Ideas Brewery and spend more time in Bennington. We loved Madison Brewery Co in Downtown Bennington. Such a cute little town!
We stayed at THIS airbnb and loved it!
We had breakfast in Manchester at Up for Breakfast and then drove to Bridgewater Corners. We had beer at Long Trail Brewery. It was quite the drive but OMG this brewery was so beautiful. It was along a river with the most gorgeous leaves!
After the brewery my mom just HAD to have cider so we drove over to Champlain Orchards. Another MUST! You can pick your own apples, raspberries, blackberries, and so much more. They had the best apple cider and apple cider donuts. They also gave us a tasting of all of the wine and hard cider they had and we wanted it all. Definitely the best hard cider we had all trip. We bought some to drink at the airbnb. The Orchards are in Champlain Valley and the drive is stunning.
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After the cider we grabbed some food in Middlebury and slept at THIS airbnb. It was amazing!
On Day 5 we drove to Burlington and did the 14 mile bike ride along Lake Champlain. Tip: Get an ELECTRIC BIKE! Unless you really like biking. It is all flat so it isn’t super tough it just takes awhile. Miller make it about 2 minutes before a total freak out so her and Troy stayed behind but he ended up having a great time with her swinging next to the lake. The bike ride was beautiful so you should definitely do it!
On the way to Burlington we stopped at the cutest Christmas shop I have ever seen. It was huge and they had so much to see. A MUST SEE on this road trip! It was called the Christmas Loft and it was in Shelburne, VT.
After the bike ride we had crepes at Skinny Pancake and Cider at Citizen Cider. Burlington is such a cute town!
We left Burlington around 6pm and drove 2.5 hours to Jackson, VT.
One of our biggest regrets was making this drive in the dark. We did it because of Miller’s sleep schedule but if you can work around it, definitely leave Burlington earlier and make this stunning drive in the daylight. When we woke up in Jackson, VT we realized what we had missed.
We stayed at Nordic Village Resort and it was WAY OVERPRICED. Again, it was the last minute so we didn’t have any other options. Apparently it was the busiest weekend of the year.
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By now we could tell Miller wasn’t feeling herself. Troy stayed behind with her again while my mom and I climbed Mt Washington on a train: The Mt Washington Cog Railway. It was a cool experience but it took three hours and we pretty much just saw fog the entire time. I would highly suggest HIKING in the area rather than doing the railway. The drive to and from the railway was completely stunning and we wished we would have just hiked instead!
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We then grabbed Troy and Miller and explored Jackson, NH. It was such a cute town that had an exhibit of pumpkin people. They painted pumpkins to make them look like real people or characters. I loved it!
We then went back to the hotel so Miller could get a good nap in and finished the night with dinner at Tuckermans.
We stayed at the same overpriced hotel!
We drove to Maine! It was only an hour and 30 minutes and the drive was so pretty. We started the day at the Cape Elizabeth Lighthouse and honestly it was a little underwhelming. Luckily it wasn’t too far out of the way and I got this super cute picture with Miller.
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We LOVED Portland. We checked into our Airbnb (find it HERE), and hit the streets! We first had lunch at Bob’s Oyster Bar. The lobster rolls were so good but the clam chowder was EVERYTHING!! Best chowder we had all trip. We then walked in all the shops in Old Town and ended the day with dinner at Street and Co. It was DELICIOUS!!
Later Troy and I watched Monday Night Football at Liquid Riot. We had so much fun there!
We stayed at THIS airbnb and it was perfect.
We drove home and only stopped when Miller woke up. The first stop was at breakfast in Kennebunkport. The second stop was at the most amazing winery called Nashoba Valley Winery. The last stop of the day was in New Haven where we had dinner on the water at Shell & Bones. We then drove all the way back to LaGuardia and stayed by the hospital. It was so hard for Miller being in the car so much that day. We tried to stop whenever she was awake and give her ample time to play and stretch her legs.
We stayed at THIS Airbnb and it was perfect for us! Right next to the airport and there was even a free shuttle bus.
Without a baby we probably would have stopped in Salem, MA and we really wanted to see the Mark Twain house in CT.
What I didn’t mention in all of those recaps were the leaves. They were like a fairy tale. Every day was an amazing adventure just driving through the leaves. I have never seen anything like it. I have been to a lot of places and have seen a lot of things and the leaves on the New England Fall foliage road trip are still at the top of the list for me. It is just something you have to see for yourself.
We also couldn’t have done it without our Lexus570 from Drive Shop. It was the best car for the drive. We had no difficulties and actually got amazing gas mileage. This car is now on my I WANT LIST.
It also may sound like tons of time in the car but everything was close together. You can actually drive the entire road trip I mentioned in like 6 hours! Isn’t that crazy? It was just a long day in the car getting back to the starting point at the end of the trip! We still had fun because we broke it up and had a lot to look at.
If you have any questions please ask me below! I also may come back and add more details as they come to me!
Sounds like an amazing trip! Would love to do this sometime with my husband.