My family and I were able to take a bucket list trip for fall break this year:
AN ADVENTURE THROUGH NEW ENGLAND!
This has been on my personal hope-to-visit list since I first saw how beautiful the leaves change in the Northern USA, which was in late high school. I can still remember how my breath caught when I saw the picture of Vermont in that magazine all those years ago, and it was surreal to experience it in person. Spoiler alert: it was even more beautiful in person. The color everywhere was just *squeeeee!* And everywhere (yes, everywhere) was just soaked in both charm and character, too. Even the gas stations looked like cottages.
After looking forward to this trip for a whole year, we packed our bags for an early Southwest flight on Friday and spent the next three days squeezing everything we could out of our long weekend before flying home on Monday. Our home base for this weekend was Boston, Massachusetts and it was the perfect spot. We were instantly in awe of the charm, beauty, and cool atmosphere all throughout the city. We stayed at the Hyatt Regency Boston for three nights, and we loved the central location and ease of walking to hot spots that it offered. We are already hoping to return here one day and spend more time walking these fun, gorgeous streets!
Our trip began in my head long before it arrived, because I spent a while combing through an itinerary that would help us maximize our time in New England and reach our goal of visiting 4 states over the 3 days we would be there. We aren't big "rule followers" when it comes to traveling, meaning that we like to hold all plans loosely. I was extra grateful for this mindset on this particular trip, because it didn't go exactly as planned in more ways than we expected. Lots of time in the car driving from state to state opened up a lot of opportunity for traffic to slow us down, and that's exactly what happened on our first full day of driving. We had braced ourselves for some traffic, but we didn't think it would be as much as it actually was, which meant that we had to pivot some of our original plans. It all worked out in the end, as it often does, and although none of us loved the extra unexpected hours in the car, we were all grateful we still got to do all that we set out to do.
Our itinerary included the following places for exploring over a long weekend, in this order:
Boston, MA
York, ME
North Conway, NH
Kancamagus Highway, NH
Salem, MA
Woodstock, VT
New England, Day One
Explore Boston
-Check into Hotel at 2 PM
-Lunch & afternoon coffee at Tatte Bakery & Cafe
-Visit Boston Public Garden
-Visit Beacon Hill & Acorn Street
-Visit Boston Common
-Stop at playgrounds throughout the city
-Dinner at Union Oyster House
New England, Day Two
Boston to Maine & New Hampshire
-Drive from Boston to York, Maine
-Visit Nubble Lighthouse
-Enjoy coffee & donuts at Beach Bliss Cafe
-Drive from York, ME to North Conway, NH
-Stroll around the charming town and explore local shops
-Have pizza for lunch in North Conway at Flatbread Co.
-Drive the Kancamagus Highway
(And get stuck in nearly six hours of traffic. Yikes!)
-Drive from Lincoln, NH to Boston
New England, Day Three
Boston to Salem, MA & Woodstock, VT
-Drive from Boston to Salem
-Explore downtown Salem
-Visit Hocus Pocus sites
-Drive from Salem to Woodstock, Vermont
-Explore Woodstock
(Stroll around downtown and visit the Middle Covered Bridge, Woodstock Inn, and more)
-Ice cream at Woodstock Scoops before driving back to Boston
-Dinner at Regina Pizza (yum!)
-Cannolis from Mike’s Pastry (double yum!)
-One more sleep in Boston
And on our final morning in this iconic city, we got up, ate breakfast at the hotel, and stopped to see Fenway Park from the outside before heading to the airport. Next time we visit Boston, we will definitely come when baseball is in season!
Every time we visit another bucket list destination I have so many emotions, and this adventure was no exception. I now want to spend an October weekend in New England every year, thank you very much. The leaves were unlike anything I’ve ever seen before — and we live in a place where we get some incredible color, too. We didn’t visit a single place that didn’t make me feel big feels, and I wouldn’t change a single thing about our trip if I could — nope, not even the massive traffic jam we got caught in.
Everything served a purpose, and I am thankful.
I am so happy we got to have this weekend and these experiences together. It was everything I hoped it would be for nearly two decades...and more.
