New England: Fall Road Trip Guide

If you want to get THE MOST out of your trip to New England, I have an awesome itinerary for a week long road trip along the East Coast. The great thing about traveling in New England is that everything is so close together. For this Houston native, where it takes 5-10 hours to just get out of Texas in any direction, this was so ideal for maximizing our time. I am going to share with you guys my exact trip details all of which I mapped out beforehand! Have I mentioned that planning trips is my number 1 hobby?! #travelnerdalert

  • TUESDAY             Oct. 16 –Boston/ Salem
  • WEDNESDAY      Oct. 17 – Salem/ Kennebunkport/ Portland
  • THURSDAY          Oct. 18 – Acadia
  • FRIDAY                 Oct. 19 – Acadia
  • SATURDAY          Oct. 20 – Bar Harbor/ Echo Lake
  • SUNDAY               Oct. 21 – Conway
  • MONDAY             Oct. 22 – Conway / Woodstock
  • TUESDAY             Oct. 23 – Woodstock
  • WEDNESDAY      Oct. 24 – Boston
new england road trip

Getting There:

Chances are the cheapest place to fly into will be Boston Logan International Airport, which is great becuase it’s the perfect place to start your New England Road Trip. If you are planning on getting a rental car, check and see if it wouldnt be cheaper to pick it up in the city as opposed to the airport.

We took an Uber to the rental car company and spent a few hours exploring Boston before we hit the road. Boston Public Garden, is a large park in the heart of Boston with a lake,benches and bridges (reminded me of central park). This happened to be next to our rental car pick up and was the perfect spot to let Sophie run around and get some energy out after a long plane ride. We then grabbed lunch at Picco which was just a short drive from the Public Gardens, very kid friendly with excellent pizza!

Where to stop?

Salem, MA:

Your first stop out of Boston has to be Salem, Massachusetts! We made sure to drive through the town and stop at 7 Gable House for a photo. Then we headed towards Winter Island Park to meet up with our family. This was a great spot to watch the sunset AND spend our first night RV camping. Bonus: We got our first view of a light house!

Bed & Breakfast in Salem

We opted not to go into the heart of Salem for dinner and found a fantastic hole in the wall restaurant/ bar to eat. Anchor Pub & Grille on 20 Cabot St, Beverly, MA 01915. Don’t let appearances fool you, the food was stellar. Honestly the best scallops I’ve ever had and the lobster was so affordable and delicious!!

Anchor Pub & Grille

The next morning we headed north along the coast towards Portland, Maine with stops in Kennebunkport along the way. When you are from the South, especially Texas, just driving in New England is a highlight in it of itself. The coastline, the colonial homes, everything just looks and feels so different. And making the drive in the fall when all the leaves are changing? Icing on the cake!

The best fall decor I’ve ever seen!

York, Maine:

We opted to drive along the coast with hopes of seeing as many lighthouses as possible. The Nubble Light House in York, Maine was under construction but still so cool. We made a little pit stop to fly the drone, during which we totally underestimated the wind, lost said drone in someones yard 2 miles away, performed a search and rescue and somehow got the drone back!!

Portland, ME:

On our way to our camping spot, we wanted to stop at the Portland Head Light. The weather had turned really rainy but it was still cool to get to see this massive lighthouse up close.

Our night was spent sleeping at Wolfe’s Neck Oceanfront Camping, right outside of Portland. Unfortunately, we didn’t get to spend much time here at all but if you do, it has so many fun activities especially for kids. There is a farm with cows, goats, chickens and ducks, a farmhouse cafe, hiking trails and best of all, you are ocean side. Aside from this the campground is beautiful and quiet with lots of trees.

Acadia National Park/ Bar Harbor, ME:

We then moved on to spend 3 days in Acadia National Park which you can read all about in my dedicated blog post. I talk all about where we slept, what hikes we did and so on. But in short, add it to your New England road trip – the leaves were at peak and it’s one of the most beautiful places I’ve ever seen.

Conway, NH:

After leaving the park, we headed inland towards Conway, NH which has the most beautiful train station I have ever seen. They offer 3 different rides, depending on what you want to see and how much time you have. We booked the one hour ride on the old steam engine which I highly recommend if you are traveling with kiddos – my daughter loved it.

Cathedral Ledge State Park is a great option if you have non-hikers or little ones with you. You can access a mile-long road which leads to the top of 700-foot Cathedral Ledge where views across the Saco River Valley to the White Mountains can be enjoyed. The park can be also be accessed from hiking trails at Echo Lake State Park. Once on the top, a new accessible hiking trail leads to a view of the valley which is completely fenced in, making it safe for little ones. The view was incredible and we did notice some people climbing the rock face – turns out both Cathedral and nearby White Horse ledges are popular rock and ice climbing walls.

One little side note about Conway – there are strict rules on where you can camp. All the campgrounds within a 20 mile radius were closed for the year, so we assumed we would sleep at Walmart ( they permit RV parking on our store parking lots). Well this particular Walmart had many signs stating no overnight camping. I went inside and spoke to a manger and they said it’s not them that enforces this rule it’s the police department. So in desperation, I called the police department and got an ok!

We ate dinner at a cute wilderness themed restaurant called the Muddy Moose which was very good and affordable. The large taxidermied Moose, fireplace and antler chandeliers made for a fun ambiance.

Kancamagus Highway:

Arguably the most famous attraction for viewing changing leaves in New England is a trip on the Kancamagus Highway. “The Kancamagus Scenic Byway takes you through a path cut through the White Mountain National Forest with breathtaking views of the White Mountains, the Swift River, Sabbaday Falls, Lower Falls and Rocky Gorge. The Kanc takes you to an elevation of just under 3,000 feet at its highest point at Kancamagus Pass on the flank of Mt. Kancamagus near Lincoln, NH.” This highway is 34.5 miles long and does offer several stopping points with restrooms and look out points but make sure you pack snacks before you go because there are no restaurants or gas stations along the way!

Woodstock, VT:

From here we made our way to Woodstock. This is the place I was most excited for on the entire trip. I just needed to see one of America’s prettiest small towns with my own eyes. And while the rain quite literally dumped on us the whole time, we spent two awesome days exploring the town library, covered bridges and little shops.

Some fun itinerary ideas:

  • Stroll downtown
  • FH Gillingham & Sons – this 1886 Vermont general store is one of the oldest in VT
  • Billings Farm – working farm & museum (great for kids)
  • Quechee Gorge – Vermonts little Grand Canyon
  • Maple syrup & cheese tasting at Sugar Bush Farm
  • Photo op at Woodstocks covered bridges
  • The Woodstock Inn – want to splurge a little? Spend the night at this gorgeous Inn.

Boston, MA:

On our last day we explored some more of Boston, exploring the beautiful campus at Harvard. We found a hole in the wall pizza spot with only 4 tables that was a favorite of Mark Zuckerberg’s when he attended Harvard. It’s called Pinocchio’s Pizza & Subs and you order at a counter in the back room where the vast menu offerings are displayed. The pizza is fabulous and it feels really cool to be surrounded by locals and students enjoying a slice.

Then we drove over to Beacon Hill area because I had to find the famous Acorn Street. One of the most photographed streets in the city, Acorn Street offers visitors a reminiscent ride back to colonial Boston. It was on this lovely street that 19th century artisans and trades people lived and today the row houses are considered to be a prestigious address in Beacon Hill. And while Acorn Street was well worth the trek, the surrounding neighborhood and shops were great to walk around in.

And just like that, after 8 days, our trip was over! This will always be one of my favorite trips because we go to see so much of New England without being stuck in the car for hours on end. We did camp but there was no shortage of beautiful BnBs that we could have stayed at. During peak fall foliage, you can stop in any small town and be rewarding with the best views. As I’m watching the leaves start to change again this year (on people’s instagram, obviously not here in Texas) I can’t help but wish I was going to New England.

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