AndiLast winter, the girls and I embarked on a New England winter road trip. We spent 9 days traveling through the New England states exploring all the fun winter activities. Our itinerary changed a couple times due to weather, but overall we had a fantastic vacation.
New England is a great road trip destination, since the states are so compact and close together. Plus during the winter, the roads are not scary like other parts of the US that get snow.
Day 1 of our New England Winter Road Trip:
We flew into Boston and was supposed to arrive around 11am, but unfortunately we had a flight delay. After arriving around 4:00, it took over an hour to get our car rental. We eventually got on the road to head to Portsmouth close to 5:30 pm.
With all the delays, we had no time to wander around Portsmouth before dark. Our original plan was to have a late lunch in Portsmouth, stroll around the historic downtown area, explore a nearby beach and then dinner.
At this point, we were exhausted. We grabbed fast food for dinner, checked into our hotel and called it a night. Not exactly a great start to the trip, but sometimes travel days are like this.
We stayed at Wentworth by the Sea, a Marriott hotel. It’s technically in New Castle, but very close to Portsmouth. Absolutely loved it! It is a charming historic hotel right on the ocean.
Day 2- Portland, Maine
We woke up early and started our drive to Portland. It was only an hour away, so we didn’t have far to travel.
We spent the morning exploring all the lighthouses around the Portland area. This is such a beautiful area and the snow really adds to the charm. Although, I’m sure they are just as beautiful in the summer too!
Portland Headlight was the prettiest lighthouse we saw in my opinion. Spring Point Ledge Light was the most adventurous one! We walked over icy rocks to get to it. The last one we saw was Portland Breakwater lighthouse. There was too much snow and ice, so we didn’t walk up to this one.
For lunch, we ate at Flatbread Company. The pizza was delish, and the view even better! It’s right on the water. For dessert, we tried the Whoopie Pie. Apparently its a thing in Maine. It’s made of chocolate, so of course I loved it.
After lunch, we walked along the East End Beach. First time I’ve ever seen snow and ice on a beach! I wanted to visit the Eastern Cemetery but it was covered in snow and we were cold, so we skipped it.
Our hotel for the night was located near Old Port, so we checked in early to ditch the car and walk around. Old Port was adorable! I love historic areas and this is one of the best! Cobblestone streets, charming shops, great restaurants and just steps away from the piers. We spent the rest of the afternoon exploring the area.
For dinner, we walked down to the pier and ate at Luke’s Lobster. When in Maine, lobster is a MUST! The grilled cheese lobster was pure yumminess. And again the views here are great!
For us Texans, we called it a night because it was COLD! We stayed at the Aloft hotel and the location was perfect! Walking distance to many shops and restaurants. They have a fun lounge and bar area that’s great to hang out in.
Day 3 of our New England Winter Road Trip
This was one of the days I was looking forward to the most, but I had to change plans last minute due to a snow storm coming in the next day.
Originally, We were going to drive to Jackson, New Hampshire and see snow sculptures from the snow sculpting competition, then head to Nestlenook Farms for ice skating. After, drive to North Conway where we would stay the night, hike to Diana’s Bath (A frozen waterfall), explore the downtown area and have dinner. The next day would include driving the Kancamagus Highway and seeing the Ice Castles in Woodstock, NH, then heading on to Burlington, VT. The Ice Castles are on my bucket list! But it did not happen this trip, so I’ll have to go back.
Instead, we drove to North Conway and explored the area for an hour or so. Then we drove the Kancamagus Highway. I’ve driven this in summer and its beautiful, but the snow makes it look like a winter wonderland!
After that, we drove straight to Burlington, VT. Checked into our hotel and had a pizza delivered from Big Daddy’s.
Day 4- Burlington, VT
We were ready to explore Burlington today! This is such a cute town, we couldn’t wait to see it. Our hotel was close to everything, so I didn’t have to worry about driving.
For a late breakfast, we ate at The Skinny Pancake. The blueberry crepes were amazing! Afterwards, we walked along Lake Champlain. There are great walking trails in Waterfront Park, although some of them were covered in snow and ice. We took a small break at the hotel to warm up a bit.
Our next destination was Church Street. Church Street is picture perfect! Like right our of a postcard! We explored several boutiques, coffee shops and bookstores. It was getting colder and started snowing, so we took frequent coffee and hot chocolate breaks.
For dinner, we ate at El Cortijo Taqueria. Considering that we are from Texas and have an abundance of amazing tacos, this place was pretty good.
In the evening, Church street is covered in lights which makes it even more beautiful! We didn’t stay to long though because it was COLD! Another early night in the hotel room.
Day 5 -Drive To Boston
Today’s plans changed as well. We were going to get an early start today to explore Stowe and go horseback riding, but the weather didn’t cooperate.
We stayed at the hotel as long as possible to wait out the snow storm, but it didn’t let up. I decided to head to Boston anyways, because I’d already booked the hotel.
The drive should have taken around 3.5 hours, but it took us 7 hours! I am from Texas and do not drive well in this weather, so I did go slow. I was keeping pace with most of the cars on the road though and I’m glad I upgraded to an SUV.
We did finally make it to Boston and stayed in the downtown area by Faneuil Hall.
Day 6- Boston
I’ve been to Boston a couple times and love it! The city is full of history, delicious food and very walkable!
Our first stop was Quincy Market. So many food options!! I tried clam chowder for the first time and liked it. It’s perfect for winter in Boston! We tried many other treats from the numerous vendors there. All good.
We walked some of the Freedom Trail, browsed through shops and explored historic cemeteries. I am fascinated by old cemeteries. There are some that have people from the Mayflower buried here! The snow covered up a bunch of the headstones, so it was hard to see the dates.
Of course, plenty of stops for coffee and hot chocolate since it was cold. We made our way to the North End area. For dinner, we stopped at La Famiglia Spagnuolo’s, because one of the employees was on the street and convinced us to come in. It’s a small Italian restaurant and we loved the atmosphere. The food was delicious as well!
Day 7- Mystic, CT
The roads were much better today, so we continued on to Mystic Connecticut. But first, we took a detour to see Louisa May Alcott’s Orchard House. The girls are fans.
Our first stop in Mystic, was the Olde Mistick Village. This is a cute shopping village with unique shops. Franklin’s General Store is perfect for souvenir shopping! They have homemade fudge, locally made jams, pickles, salsas, syrups and more. Plus candles, books, glassware and fun jigsaw puzzles.
Another favorite was Cloak and Wand. This is perfect for Harry Potter fans! It’s a wizarding shop with a potion bar. They sell magical items, books and apparel. The potion bar serves custom hot chocolates and sodas. Since they are not affiliated with Harry Potter, they do not serve butterbeer. They do have a delicious substitute! We strolled around here for a couple hours.
Mystic is the cutest city! We enjoyed just driving around and looking at the scenery. Our next stop was downtown Mystic. We explored here for a couple hours before heading to dinner. We are big Julia Roberts fans, so we had to eat at Mystic Pizza for dinner! The pizza was delicious and I loved the atmosphere.
We stayed at the Mystic Marriott Hotel. The hotel was fantastic. Very clean and staff was great.
Day 8- Newport, RI
Before leaving Mystic, we had brunch at Rise. It’s located in the downtown area. The food was great!
Next, we headed to Newport. The number one thing I wanted to do was the Cliff Walk. The Cliff Walk is located on the coast. The views here are amazing! One side is ocean and the other side are huge mansions! Some of the mansions are open for public paid tours. It was cloudy today, but I bet sunset would be phenomenal! We did not do the entire 3.5 mile walk, but did do a good portion.
After the Cliff Walk, we checked into our hotel. Our hotel was located in downtown within walking distance to shops, restaurants and attractions.
Newport’s downtown area is charming too! More cobblestone streets, charming buildings, unique boutiques, lots of food options and on the water! We strolled through downtown for a couple of hours and explored the wharf area. Then had dinner at Gas Lamp Grille.
Day 9 on our New England Winter Road Trip
It’s our last day and I decided to add on Salem , since the girls had never been. Salem is a bit of a detour from Boston where our flight was leaving, but we had plenty of time.
For breakfast, we stopped at the cutest little diner on the way. The Little Depot Diner is a renovated train car in Peabody, MA. The food here was delicious!
Then it was on to Salem. I’ve been here before and liked it. Today, not so much. I’m not sure if it’s because it was winter or covid, but hardly anything was open. Definitely a wasted trip.
Then it was on to the airport to fly home 🙁
Overall, we had a fabulous time on our New England winter road trip. I enjoyed exploring the area and hanging out with my girls. We do not have a true winter in Dallas, so being in real snow was incredible. The New England area is fairly easy to navigate even in snow storms. I did not have to deal with snow chains or steep mountain roads.
There are things that I still need to do, so I’ll be back for more winter fun. And summer fun. And fall fun 🙂
