New England
Summer road trip. Nine days. Four states.
New England Road Trip
New England has always been on my short list. My grandparents took several long road trips up the New England coast when I was a kid, and I was mesmerized by their stories and photos.
So, when we began looking for a cooler location for our summer family vacation and someone mentioned New England, it took me about 30 seconds to realize we had found a winner. Not only did this destination elicit childhood nostalgia, it also has so many wonderful things to offer - early American history, gorgeous mountains and beaches, unique local cuisine, and no shortage of family-friendly adventure.
My first step in planning any trip is to check out other travel blogs, and I found some really amazing ones for the New England area. And then I stumbled upon “The Best 7 Day New England Road Trip Itinerary (+ 5 & 10 Day Options!) 2023” by New England Wanderlust. With a very few personalizations, her itinerary was perfect for what I wanted for our family vacation.
Day 1 - Travel and Boston
As a general rule, I don’t schedule activities for travel days. Flight delays, lost luggage, traffic jams - there are too many variables.
But this was our lucky day, and we ended up in Boston and checked-in to our hotel with plenty of time to explore the area around our hotel.
Planning for ease of exploration, we stayed on Boston Harbor right on the Freedom Trail near Bunker Hill. This made an impromptu visit to the USS Constitution in Charlestown Navy Yard at the Boston National Historical Park possible before we grabbed dinner at Warren Tavern, the oldest tavern in Massachusetts.
The amazing thing about walking down the streets of Charlestown, the oldest neighborhood in Boston, is we were immediately transported back in time. We dined were George Washington and Paul Revere mingled with other early American figures. We followed the red-brick path of the Freedom Trail past a Revolutionary War battleground, federal-style homes, historic plaques, and more.
Our “travel day” ended up being packed with lots of history and adventure!
Day 2 - Woodstock, VT
We started Day 2 with a little over two-hour road trip to Woodstock, VT, and although it started off gray and wet, we didn’t let that dampen our adventuring spirits.
The rainy morning was perfect for ducking in-and-out of the locally-owned shops to find some uniquely Vermont products. Some of our favorites were FH Gillingham & Sons with 130 years of history selling Vermont goods; Yankee Bookshop, Vermonts longest-running independent bookstore; The Vermont Flannel Store with products made with 100% GOTS Certified Organic Cotton; and Mon Vert Cafe for delicious treats made from locally-sourced and organic ingredients.
For such a small town, Woodstock is packed with a variety of activites that are sure to please everyone in your crowd. Because we were only planning one day here, we had to narrow it down.
I don’t think you can go to Vermont and not see a covered bridge. In the pedestrian-friendly village, we didn’t have far to walk to find the charming Middle Covered Bridge, one of four covered bridges in the area.
For the afternoon, we headed just a half mile north of Woodstock to the Marsh-Billings-Rockefeller National Historical Park and Billings Farm & Museum. With adjoining properties and history, these two partner properties highlight the vast beauty of Vermont due to their long-standing focus on conservation and land stewardship. After touring the Marsh-Billings-Rockefeller Mansion, exploring the gardens, hiking the grounds, and completing the Jr. Ranger program at the park, we headed over to the farm where learned about 19th and early 20th century farming, enjoyed a maple sundae from the Farmhouse Scoop Shop, and fell in love with adorable baby farm animals. while we managed to see all of this in one afternoon you could easily spend a whole day exploring one of these fascinating sites.
Day 3 - White Mountains, NH
We could not be this close to King Arthur's Court Bakery and not stop for breakfast! So, we started day three with a slight (and delicious) detour on our way to New Hampshire.
With full bellies, we headed through the gorgeous White Mountain National Forest on the way to our next stop, the Flume Gorge in Franconia Notch State Park. The moderate 2-mile loop which goes through this natural geological marvel is breathtaking, and took us about an hour and a half. The path also took us over two more adorable covered bridges (I may be slightly obsessed).
After our hike, we headed to Polly’s Pancake Parlor in Sugar Hill to refuel. This place is the real deal. When we got there the wait for a table was an hour and 45 minutes on a weekday, and it was 100% worth the wait. If you are a fan of breakfast and you are anywhere close to the place, make sure you stop by.
After lunch, we headed to the summit of Cannon Mountain via North America's first Aerial Tramway. Known for its excellent skiing and snowboarding in the winter, Cannon Mountain also offers some gorgeous hiking and views year round. At the top we trekked up a short trail to the observation tower which provided amazing 360-degree views where on a clear day you can see New Hampshire, Maine, Vermont, New York and Canada.
We wrapped up our afternoon in New Hampshire visiting Littleton, a quaint little town with charming shops, restaurants, brewery, and street art. The boys enjoyed visiting the world’s longest candy counter at Chutters. We did a little shopping at Lahout’s, America’s oldest ski shop. And of course we visited the Little Village Toy & Book Shop, because, well, we can’t miss a bookstore! Speaking of books, one of my favorite spots in Littleton was the Pollyanna Gateway, which is adorable art installation of colorful umbrellas that celebrates hometown favorite, Eleanor H. Porter, the author of Pollyanna.
Day 4 - Bar Harbor, ME (4th of July)
I realize there are some really cool places around the country to celebrate the 4th of July, but in my opinion, Bar Harbor has to be one of the best! This would probably be a good time to tell you that we planned this entire trip around being in Bar Harbor for the fourth, and, y’all, it was everything we dreamed of!
Situated on Mount Desert Island, Bar Harbor is known as one of the best summer vacation spots in the country. The Today Show has voted Bar Harbor’s Fourth of July celebration #1 in America, and it lives up to that reputation.
The schedule of events of the day literally goes all day! We drove into town just in time for their Independence Day Parade, and we joined the red-white-and-blue clad locals in cheering and waving as the bands, cars and trailers slowly drove through. After the parade, we visited the Craft Fair/Marketplace hosted by the Island Arts Association and then crossed the street to the Bar Harbor Athletics Field for the The Bar Harbor Rotary Club’s Seafood Festival, where we had our first Maine lobster roll. While we waited for the live music at the Town Pier and the Bar Harbor Town Band to play, we ducked in and out of many of the cute shops on Main Street including Acadia Trading Post, Sherman's Maine Coast Book Shop, and the boys’ favorites, Cool as a Moose, and Bark Harbor. We also had a delicious dinner at Side Street Cafe, which was a couple of blocks off Main Street, so not quite so busy before we headed down to Agamon Park for the big finale - Fireworks Over Frenchman Bay.
Day 5 - Acadia National Park
We have loved using our Every Kid Outdoor pass this last year, and since it expires on August 31, we wanted to try to use it another time or two before then. If you don’t know about this program, it provides an annual pass to fourth graders, and they can use it to visit national parks, wildlife refuges, marine sanctuaries, and forests with their famlies for free.
I am not sure I have the words to describe how beautiful Acadia National Park is. Because we only had one day in Acadia, we focused on the east side of the 47,000 acre park. We took the scenic Park Loop Road to Ocean Path Trail which runs between Sand Beach and Otter Point. This trail offers some spectacular views of the Maine coast line, and is the home to Thunder Hole, one of the park’s most popular destinations. It is worth mentioning here that during peak season traffic is slow and parking all over the park is at a premium, so know you will need a good deal of patience and be able to do some walking to get to your destination. Or consider using the free (with your entrance pass) Island Explorer shuttle that provdes service to 11 different routes around the park.
After our morning hike, we wandered over to Jordan Pond to find some lunch. The Jordan Pond House restaurant recommends reservations which are very difficult to get in peak season, so we had planned to grab a bite from Carriage Road Carry Out which offers grab and go items. This area offers a variety of hiking gorgeous hiking options, so after lunch we set out on the Jordan Pond Path. This path not only circles around Jordan Pond, but it also offers views of the cliffs where the parks well-known residents, the peregrine falcons, nest.
Our last stop in the park was the Day Mountain Loop horse-drawn carriage tour with Carriages of Acadia. This horse-drawn carriage ride explores some of the 45 miles of carriage roads built throughout the park by John D Rockefeller, Jr and his family. Still today, motorized vehicles are prohibited from using these roads which are reserved for horses, bicycles and pedestrians. These roads were built along the curves of the land atop large granite blocks. The engineering of these marvels is such that little maintenance or repair has been needed since their constuction of the carriage roads between 1913 and 1940. If you decide to see the park in this fun and unique way, make sure you get directions from their website or by giving them a call before you head that way. Cell phone reception is really spotty in the park, and you will not be able find them using your GPS.
Day 5 - Bar Harbor, ME
Our last night in Bar Harbor we booked the evening Lulu Lobster Boat Tour. Y’all, it is an understatement to say we had a blast on this tour! First of all, the tour is relatively small because they take you out on an actual traditional Downeast-style lobster boat. On our 2-hour tour (cue the Gilligan’s Island music) our amazing tour guide, Jen, packed in awesome harbor views, a lighthouse, baby seals, dozens of stories from the past and the present about the area and it’s people, and, of course, all things lobster related!
Not only did our captain take us through the entire process of catching lobsters, the boys also got to hold the freshly-caught lobster! In addition, we learned a whole slew of lobster facts that we didn’t know. Here are just a few of the things we now know about lobsters thanks to our Lulu Lobster Boat Ride:
They pee from between their eyes as a defense mechanism (yes, one of our boys got peed on).
They can regenerate all of their body parts except for one - their eyes. If they lose an eye they regenerate something else in its place instead (a claw, etc).
Female lobster carry their eggs ON (not in) their stomachs, and they are pregnant for 18-24 months.
They swim backward and one flick of their tail can send them soaring backward 25 ft.
They don't have teeth. They chew with their first stomach. They have two.
They can live out of the water for up to two days.
Their blood is clear.
If you are anywhere near Bar Harbor, please take this tour. I promise you will not be disappointed!
Day 6 - Portland, ME
Before we left Mount Desert Island, we were able to get a highly-sought-after ticket for sunrise on Cadillac Mountain. First things first, getting tickets. When I say highly-sought-after, I am not kidding, but visit our blog post for some tips that will help you out.
We got up at 3:40 a.m. to make it to the summit before the 4:54 a.m. sunrise. Sunrise on Cadillac Mountain is a bucket-list item for a lot of people. The summit is the highest point on the eastern seaboard making it one of the first place to see the sunrise in the US. Watching the sun peak over the horizon was a breathtaking array of pinks and yellows and blues. This was definitely an experince and a memory that we will be talking about as a family for a very long time!
After such an early start to our day, once we made it to our next stop, Portland, ME we needed a lower-key day. Our first stop in Portland is Portland Head Light and Fort Williams Park. The park houses Maine’s oldest ligthouse, commissioned by George Washinton in 1791, Portland Head Light is one of the most photographed lighthouses in the US. This visit is a two-for-one deal, as you can also see the Ram Island Ledge Lighthouse from the shore.
For lunch we ate at Shay’s Grill which serves upscale pub food and is famous for their hamburgers. Hubby ordered “Coop’s Hot Chicken” and said it was every bit as good as Nashville hot chicken!
We spent the afternoon exploring Old Port a historic area known for its shopping, restaurants, piers, and cobblestones. And we were lucky enough to stay just blocks from the Portland Observatory which is perched atop Munjoy Hill giving it a clear view of Portland Harbor.
Day 8 - Boston, MA
You may have noticed that we skipped day 7. We ended up spending a day in our hotel room with illness. While we missed a few things we really wanted to do, but thanks to travel insurance, we were able to get most of our money back.
Luckily, by the afternoon of Day 8, we were able to attend the Boston Red Socks v. Oakland Athletics at the oldest MLB ballpark, Fenway Park. It was a beautiful afternoon for a game, and not only did Red Socks win, but we were even able to see a couple of homeruns hit over the Green Monster.
We are already planning a weekend trip back to Boston to do the things we missed - the Salem with Beth tour, the Freedom Trail Walking tour, Paul Revere’s House, the Old North Church, and the Boston Tea Party Ships & Museum. So, check back for future posts about that trip!