Disclosure: This post on how to plan a New England road trip is sponsored by Moon Guides, but all thoughts and opinions are my own.
If there’s one method of travel getting a major resurgence this year, it’s the road trip. Just in time for your Fall road trip planning, Moon Guides has released . Although the book came out today, team Ready to Stare was lucky enough to get an advanced copy. We used this as travel guide to take a New England road trip.
The Open Road features 50 different road trips in the United States. With flexible itineraries, this travel guide includes everything from weekend trips to cross-country jaunts. The Open Road breaks each trip down by region. You can explore three cross country trips or take a gander through trips that cover California, the Pacific Northwest, the Southwest, Rocky Mountains, the Great Lakes, New England, the South, Alaska and Hawaii. 50 states and enough road trips that could have you checking every singe one off your list!
The book’s author Jessica Dunham is an experienced road-tripper so like all Moon Guides books, you can be sure the advice is unbiased and based on personal favorites. Whether you are traveling with your family or your partner, there’s something for every kind of traveler. There’s even playlist suggestions in case you need a break from podcasts. Consider this your guide on where to go, what to do while you’re there and where to stop on the way.
Being located in the Midwest, we had so many choices for a road trip route from The Open Road. We could drive east to New England, south to Kentucky’s Bourbon trail or west on Route 66 from Chicago to Los Angeles. Since we just traveled , we decided on the Best of New England road trip. Fall is when the east coast really shines so this seemed like perfect timing. We knew we want to add a stop to Salem, Massachusetts and the Best of New England itinerary made it easy to make time for a little spooky.
Moon Guides’ Best of New England road trip is a 14-day itinerary starting in Boston. We only have nine days to travel and rather than flying into Boston, we opted on driving from Cleveland. We used the map in The Open Road to plan our stops adding a few and taking away others that we didn’t have time to drive to in our shortened trip.
The ability to customize your trip is one of the things I really loved most about planning a trip using The Open Road. Here is our New England road trip itinerary. LA Carr of created the video and all images seen here.
Day 1: New Haven, Connecticut
The Best of New England road trip starts in Boston. Since we were driving from Cleveland, we decided to start by driving to Connecticut. We picked New Haven based on distance. It was about an eight hour drive from Cleveland to Connecticut. After doing multiple 15+ hour driving days on our last road trip, we wanted to minimize any drive longer than eight hours.
Leaving early in the morning and only having to drive eight hours, gave us time to explore a few different places in Connecticut. We went to the iconic in Noank, CT to take pictures and walk around.
We headed next to Mystic for some pizza. The famous Mystic Pizza didn’t have any outdoor seating so we opted for salads and slice at . We ended the evening with dessert and an iced maple lattes from
Day 2: Salem, Massachusetts
On our way out of the New Haven area, we grabbed coffee at . In the theme of keeping it spooky, we made a pit stop at the Seaside Sanatorium in Waterford, CT. This building was first constructed as a medical facility to treat children with tuberculosis.
Over the years, it served the elderly and people with mental illness. It officially closed in 1996 following years of patient abuse allegations. With this history, it’s no wonder this now state park still gives visitors the heebie jeebies.
Once we arrived in Salem, Massachusetts, we drove right past to the next town over to check into , a small hotel in Beverly that we originally found via AirBnb. With a king bed and a twin bunk bed lofted above the bathroom, our room was perfectly cozy and perfectly located right around the corner from Salem for a fraction of the cost.
In Salem, we started with an outdoor-only tour at the . Originally built in 1668, the House of Seven Gables remains one of North America’s largest timber-framed mansions still standing on its original foundation. After our tour, we headed across the street to the country’s oldest candy company, for some fudge and classic candy.
We stopped next at the Salem Witch Trials Memorial. Constructed in 1992, the granite benches memorialize the 20 lives lost in the 1692 Salem Witch Trials. The memorial sits right outside the Old Burying Point Cemetery.
We made a private shopping appointment at . This store is the definition of modern metaphysical. With art proclaiming “Black Trans Lives Matter” on the wall and mugs that say ‘they/them, HausWitch truly felt like an inclusive space to practice self care.
Due to Covid, an appointment is required at HausWitch to minimize contact. We also had to wear gloves inside the store. Everywhere in downtown Salem inside and out is a mandatory mask zone. This personally made me feel safer to walk around on busy sidewalks. Most stores has strict limits on how many guests could enter.
Day 3: Gloucester, MA / Salem, MA
About a 30 minute drive from Salem sits Gloucester, MA. We headed there to go on a three-hour whale watching tour. I had never been whale-watching before so I didn’t know what to expect. But there’s few things in life that I can say compare to seeing a whale pop up from the ocean in real life. This is a must for any New England road trip taken between April – October.
We took our trip with and the guides passion for whale conservation really impressed me the most. There was someone on our trip with us specifically to catalog and report back which whales we saw, where and at what time. Since whales have unique tales, the North Atlantic whales all have names. Some of them have been tracked in that part of the ocean for 45 years.
After our whale-watching high, we took a quick drive through Manchester-by-the-Sea before heading back to Salem. As big Hocus Pocus fans, we had to visit the sites from the movie.
We first went to Old Burial Hill Cemetery in Marblehead, MA. This is the cemetery from the beginning of the movie where Max loses his sneakers to Jay and Ice.
We next went to the Hocus Pocus house aka Max and Dani’s house. It’s located on the gorgeous Ocean drive. The current owners sat on the porch and we snapped excited photos along with the other tourists. I don’t know how many guests they get per year visiting their home, but I would venture it’s a lot.
We ended our day with a Pickle Rick pizza at . Yes, that’s exactly what it sounds like! A pizza with pickles.
Day 4: Provincetown, MA
If there’s one place I’ve been wanting to visit since , it’s Provincetown, MA. This seaside town is one of the US’s most famous LGBTQ+ travel destinations. The Open Road suggests hitting PTown on your way back on Day 12 and 13. We opted to hit it on our way up North to Maine.
We started our exploration of Provincetown along Commercial street as The Open Road suggested. From feminist book stores to queer art galleries, walking Commercial Street from Montello and Howland Street allowed us to take in the main center of the town’s charm.
We stumbled upon a beach with a rainbow flag and I couldn’t resist kicking my way through the Atlantic ocean for the first time all 2020. Provincetown really felt like a place where I could be myself and just relax.
My favorite find along Commercial Street was . I love ALL things Christmas. I know this trip was supposed to be Halloween themed, but I couldn’t resist stopping in and grabbing an ornament or 10 from Monty’s Christmas. The atmosphere was amazing and the shopkeeper was a true gem.
For a late lunch, we took a suggestion from The Open Road and hit up When I tell you these were some of the best fries I’ve ever had! The food was amazing but the view was even better. Picnic tables sit almost right on the beach.
On our way out of PTown, we stopped for a view of the Nauset Light as The Open Road suggested. It’s true that this view of the ocean cannot be beat. On a warm day, we could see how this would make for a perfect walk.
Day 5: Boston, MA / Portland, ME
Although The Open Road suggests starting your trip in Boston, we opted on skipping any major cities due to Covid. Moon Guides suggested we check out the Freedom Trail so we stopped by the Charleston Navy Yard to snap a few pictures. We waved at the Bunker Hill Monument from the car before making our way up to Portland, Maine.
On our way, we stopped at a roadside attraction in Lincoln, MA. It’s a bunch of old rocking horses in a circle. I don’t know why it’s there but at least they were pro-Biden!
Once we arrived in the Portland area, we took a tip from The Open Road and stopped for lunch at in Cape Elizabeth.
We enjoyed a classic lobster roll and took in the amazing view of the crashing waves below and two different light houses in the distance. Beware of the seagulls. They are bold and they WILL steal your food.
Next we went to Portland Head Light, another Moon Guides suggestion. This lighthouse you can actually get right under. We enjoyed a bit of gelato while exploring this area.
Day 6: Portland, ME to Acadia National Park
We started our morning with donuts at Holy Donut. The Open Road said this was an essential breakfast stop in Portland and the 30-minute line we waited in for donuts showed we weren’t the only ones wanting in on this sweet potato donut action. These did not disappoint.
After breakfast, we started the drive to Acadia National Park. It was a rainy day which sadly soured any good view atop the famous Cadillac Mountain, the first place you can see the sun rise in the United States.
As we drove around Acadia, we stopped at Sand Beach. This was one of the most beautiful sites on our entire trip. With views of both the forest and the ocean waves, this view was like nothing I had ever seen before!
We stopped at Bar Harbor for some souvenirs before driving back to Bangor where we were staying for the evening.
Day 7: New Hampshire
On the seventh day of our trip, we had planned to drive from Acadia National Park to North Conway, New Hampshire as The Open Road suggested. We planned on driving to the top of Mount Washington and hiking to Diana’s Bath. The Open Road sold us on these sites but Mother Nature had other plans.
With the rainy weather and slippery roads, we opted on heading south through New Hampshire to our next destination in Vermont instead for a smoother drive.
Day 8: Brattleboro, VT
Our entire drive through Vermont was all winding roads with not a highway in sight. This allowed us to really take in the fall foliage that you would expect from a New England road trip.
We stopped in Grafton to try some cheese at Grafton Village Cheese Company but they were closed. Luckily, there was a cute covered bridge that was a perfect photo spot.
Down the road in Brattleboro, we found the second location of the Grafton Village Cheese Company that was open. Talk about fancy! From the finest maple syrups to decadent cheddar cheese, this spot is a foodie’s dream.
Next, we.visited Scott Farm Orchard. This farm is situated on the scenic former home of Rudyard Kipling. We found this suggestion in The Open Road’s “New England for Families” section.
We picked fresh apples from the tip-top of the trees. Upon exploring the grounds, we found a pumpkin patch. We finished our visit with apple cider!
We stayed at the cutest AirBnB in Dover, VT. Upon check-in, our host Ron, took our temperatures. He showed us the cleaning supplies and provided masks and hand sanitizer if we needed it.
After chatting with Ron, we learned he is a fellow member of the LGBTQ+ community, a ski instructor and an amazing amateur photographer. We cannot recommend staying with Ron enough if you are traveling to Vermont.
Day 9: Woodstock, NY
Since we were driving back to Cleveland rather than flying in and out of Boston, we added a stop in Woodstock, New York to our New England road trip. While others may make a pilgrimage to Woodstock because of the iconic music festival, I wanted to go so I could stay at
This four-room boutique hotel is a gem of the Catskills region. Every detail feels so thought-out. When I learned that June Peterson, one of the inn’s co-owners, started out her career in hotel management cleaning rooms, it made sense why everything was so functional and yet, still aesthetic. We will be doing a full length review of our stay at The Herwood Inn so stay tuned for that!
Woodstock as a town was exactly the hippie haven I expected. Quaint coffee shops and plenty of stores with tye dye tees.
Final Thoughts
You have a lot of options when you’re planning a road trip. It can be challenging to plan a route that fits your time frame of travel. Bottom line: travel guide is one of the best ways to plan a United States road trip. We visited places we would’ve never thought to visit. Some of our best meals came courtesy of The Open Road and definitely the most iconic New England views.
Grab your copy of now and let us know in the comments below where you would like to see the Ready to Stare team travel to next!