50 State Journey- The Ultimate New England Fall Road Trip

Our family is attempting to travel to all 50 states through creative road trips. We prefer to choose a route which may have several destination stops throughout the trip. This often results in spending a short amount of time in one city. We love to get the flavor of the place that we are visiting by experiencing dining experiences, seeing a well-known icon from that area or simply experiencing the understated charm of that particular area.

For our Fall Break 2024, we visited six new states as a family. We visited Vermont, New Hampshire, Maine, Massachusetts, Rhode Island and Connecticut. We hope to visit again to spend more time in each of these beautiful states. Indiana is our home state so the below itinerary outlines how we did this memorable New England trip.

Here is how we did it!

Day 1: Flight from Indiana to Burlington, VT (layover in Philadelphia) Explored Vermont and drove to New Hampshire. Overnight in Franconia, NH.

Day 2: Explored New Hampshire and drove to coastal Maine. Overnight in Ogunquit, ME.

Day 3: Explored coastal Maine (Ogunquit and Kennebunkport.) Overnight in Rockport, Massachusetts.

Day 4: Whale watching, visit in Salem, MA and travel to Boston. Overnight in Boston.

Day 5: Explored Boston and drove to Rhode Island. Overnight in Middletown, RI.

Day 6: Explored Newport, RI. Drove to Mystic, Connecticut. Overnight in Mystic, CT.

Day 7: Explored Mystic, Connecticut. Ovenight in Coventry, RI.

Day 8: Drove to Providence, RI. Flight from Providence, RI to Indianapolis, IN. (Layover in Chicago.)

Day 1: We began our trip with an early morning flight from Indianapolis. We arrived in Burlington, VT mid-morning. We picked up our rental car. We rented through Avis and felt like they had reasonable rates for a one-way car rental (meaning we were picking up from a different location as drop-off location.) We spent time exploring Burlington and tried authentic Vermont maple syrup. We drove through Stowe, VT and made a stop for maple creemees. We then traveled to New Hampshire. We made a stop in Littleton, NH and headed on to Franconia. We had plans to stay at the Best Western White Mountain Inn in Franconia. The stay at the Best Western was great and this inn was tucked into the beautiful scenery.

We were lucky and hit the peak of the fall colors. The fall foliage in Vermont and New Hampshire was amazing!

Day 2: On Day 2, we took in more of the New Hampshire beauty by taking an aerial tram to the top of Cannon Mountain. We spent some time exploring the top of the mountain. After returning to the bottom of the mountain, we explored the White Mountain Natoinal Forest. There were so many breathtaking stops!

After our time in New Hampshire, we drove to Ogunquit, Maine where we stayed at the Colonial Inn.

All of the details of our time in New Hampshire and Vermont can be found at A Storybook Fall Trip- Our time in Vermont and New Hampshire.

Day 3: On this morning, we walked the Marginal Way cliff walk. The views were stunning. The walk is an easy walk that ends at Perkins Cove. We stopped at some boutiques and did some window shopping. We explored some shops in Ogunquit and then drove to Kennebunkport. We had lunch and took in the sights in Kennebunkport.

That evening we drove on to Rockport, Massachusetts. We stayed at the Rockport Inn and Suites.

All of the details of our time in Coastal Maine can be found at Maine- Lighthouses, Seafood and Scenic Views.

Day 4: This morning, we started our day with a whale watching tour through Cape Ann Whale Watching . We had such a fun experience! We purchased our tickets at a discount on Groupon so here is your reminder to always check Groupon when traveling. I would highly recommend Cape Ann Whale Watching. Keep in mind that it is quite chilly out on the water depending on the time of year that you go.

After finishing the whale watching tour, it was time to head towards Boston. Our trip was in October so we decided we need to visit Salem to check out the festivities. October in Salem is definitely worth a stop. We got lucky by visiting on a weekday afternoon which resulted in it being less busy. We took pictures in front of some of the iconic buildings from Hocus Pocus and learned about the history of the Salem Witch Trials.

After touring Salem, we drove on into Boston. We drove around finding our hotel and were able to see Harvard. We stayed at the Homewood Suties by Hilton Boston/ Cambridge- Arlington. As we were arriving, we discovered that Homewood Suites have a "Welcome Home Reception" which offers drinks and light appetizers. We grabbed a bite to eat and went to relax in the hotel room. It had been a very full day.

Day 5:   The next day, we had breakfast at the hotel and then headed out to explore Boston. We followed the Boston Freedom Trail on our own It was really amazing to see all of the history in this one city. We toured Paul Revere's boyhood home. We continued on our walk and made it all the way to the Boston National Historic Park to see the USS Constitution. We definitely got our steps in on this day! In fact, it was now getting later into the evening so we opted to take a Lyft back to the car as daylight would be dwindling by the time we made the long walk back.

We loved our day in Boston, but it was time to hit the road as our next hotel was in Newport, Rhode Island. That night, we stayed at the Howard Johnson by Wyndham Middletown Newport Area.

All of the details of our time in Massachusetts can be found at Massachusetts-Whales, Witches and Wayfaring.

Day 6: On this day, we visited the Newport Mansions. We investigated ticket packages and chose to visit three mansions. It was so fun to feel like we were stepping back into the gilded age. We all enjoyed visiting these intricate mansions. After lunch, we were able to walk toward the waterfront and explore the wharf area. It was fun to see boats in the water. There were also several boutique shops to explore which was fun for some window shopping.

After a late lunch and some exploring, my girls decided that we must try to find Taylor Swift's house. We drove to the Watch Hill neighborhood and were able to get a peek. It was fun to see a more modern "mansion" after our day exploring the gilded age mansions.

That evening we traveled on to Mystic, Connecticut. We were staying at The Quality Inn Mystic- Groton.  

All of the details of our time in Rhode Island can be found at Newport, Rhode Island- Chasing Starlight and Mansions.

Day 7: We started our morning by visiting B. F. Clyde's Cider Mill. This was such a fun time and fit right in with all the fall vibes. This mill is the oldest steam-powered cider mill in the United States. We were able to see a demonstration on how the machine works and how apples are turned into cider.

After visiting the cider mill, we wanted to tour the Mystic Seaport Museum. There was so much to see at this museum. We saw a variety of boats, learned about the history of seafaring and visited the historic seaport village. The views of the water or beautiful as well.

After lunch, we visited some of the shops in the Olde Misticke Village. I had read about a tea shop in the Village called "Alice in the Village" that we were eager to try. This shop is so fun and a must-see for any little (or big) kids in your life. When you enter the shop, you really feel as if you have entered Wonderland.

After our time exploring the shops, we left Mystic and spent the night in Coventry, Rhode Island. We stayed at the Holiday Inn Express as we had an early flight home in the morning leaving from Providence, RI.

All of the details of our time in Connecticut can be found at Mystic, Connecticut- Sips, Ships and Shops.

Day 8: We returned the rental car and prepared for an early morning flight home. We flew from Providence, RI to Indianapolis (with a layover in Chicago.) This New England fall trip was so enchanting. So many memories made with my family!

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