We had the most amazing fall trip to Boston!! The New England leaves are so dreamy and the weather was amazing. We were very lucky to have some of our dear friends, who are locals, to show us around for a couple of the days.

In this post, you will find details about walking The Freedom Trail (with our local friends to guide us), exploring the best lighthouses in Maine, and visiting historical sites such as North Bridge at Concord/Lexington, Salem Witch Memorial, and so much more!

(Big shout out to Brent Alldredge - best travel guide ever!)

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Day 1 - Boston: Freedom Trail

We flew into Boston midday. This is our itinerary from our local friend, Brent. I’m including our timed schedule of this day along the Freedom Trail so you can see Realistic time frames at different locations:

12:30pm Meet at Boston Commons Frog Pond

Boston Common - America’s oldest park- is a large green space park in the middle of downtown, right next to the Massachusetts State House, with gazebos, play areas, and a charming pond.
You can find metered parking around the park, or you can try the Boston Common Garage at Zero Charles Strees near the park

1pm Boston Common - Begin Freedom Trail

When you take The Freedom Trail, you are literally walking along the streets of Boston, with museums, churches, historical buildings, burial grounds, and other places of significance here and there as you making your way through town. There is a line on the sidewalk to guide you. You can join a tour, hire a guide or take an audio tour. We were blessed to have our friend guide us.
One of my favorite places along The Freedom Trail (not far from Boston Common) was the Granary Burial Ground founded in 1660. You will find John Hancock, Paul Revere, Samuel Adams and other historical figures put to rest there.

2pm Quincy Market - Freedom Trail

Quincy Market is a really fun place to grab a bite or find some souvenirs to bring home with you. There are lots of shops, a food hall and restaurants. We found a fun stuffed animal lobster to bring home for our daughter among other things.

3pm North End - Freedom Trail - late lunch/early dinner

Strolling through the North End was like walking through a story book. So many places you could stop like the Old North Church (Boston’s oldest church is best known for the midnight ride of Paul Revere)
We stopped for dinner here at an Italian place, and grabbed pastries at a local bakery for dessert

4:30 USS Constitution - Freedom Trail

USS Constitution is the oldest commissioned naval ship in the world. Nicknamed "Old Ironsides" during the War of 1812. Once a year they take it out and still sail it around.

5:30 Bunker Hill - End of Freedom Trail

We finished off at Bunker Hill, the place of the first major battle of the Revolutionary War. We explored here for about half an hour.
It was quite a walk from here to Boston Common where our cars were parked, so we took an Uber from here back to our cars. From there, we made the drive to our lodging for the night.

Day 2 - Visiting Lighthouses in Coastal Maine

One activity we didn’t want to miss, was visiting lighthouses in Maine! We drove from Boston, through New Hampshire, up to Maine and saw the most Gorgeous terrain on our Journey!

12 noon - Portland Head Light - Cape Elizabeth, Maine

Portland Head Light is the oldest lighthouse in Maine. It’s situated on the shores of Fort Williams Park, Cape Elizabeth.
This is about a two hour drive from Boston. We did the longest part of the drive first, and then worked our way back as the day went on.
We climbed over a rope to explore, take pictures and hike along the rocky shore. We spent about 30 minutes exploring here.

1:30pm Nubb’s Lobster Shack at Cliff House, Maine

This is a casual, New England style restaurant in Cliff House. It has the most breathtaking view of the Atlantic Ocean. We dined outside on the picnic tables and relished in our gorgeous surroundings.
We tasted lots of tasty foods here, but our favorite was the lobster rolls (lobster sandwiches - much better than just the plain lobster) and crab rolls. While in Maine, we had to have lobster, right?!!

2:45 Nubble Lighthouse - Maine

This was a smaller, but also beautiful lighthouse in Cape Neddick. Only about 15 minutes from Cliff House. We spent about 30 minutes here exploring and taking pictures. It’s about an hour and a half from Boston.

5pm Bedford Farms Ice Cream in Bedford, Mass

BEST Ice Cream!!!! It’s locally sourced and incredible. It has awards for being the best ice cream around, and they definitely live up to the hype! We visited this shop twice on our trip, it was so good! My favorite flavor was the Raspberry Chocolate Chip - AMAZING!!

Day 3 Boston - Salem - Rockport

These are all places suggested by our local friends. we explored on our own, at our own pace.

9am Breakfast at The Farmhouse Cafe - Dunstable, Mass

This was the most delicious meal of the trip!!!! This was our farewell breakfast with our fabulous guide, Brent. Everything we ordered was absolutely incredible. It was quaint and so charming! I am still dreaming of the mouthwatering Pumpkin French Toast!

11am Salem, Mass

We learned very quickly in Salem, that we should’ve booked tickets ahead of time for different activities in town, such as the Salem Witch Museum. Most everything was sold out, with it being the month of October. It was packed with visitors, even on a weekday.
Parking was also tricky when it was that busy, but we were able to locate a large parking garage within walking distance of downtown. There are also free shuttles you can take in October, but they run on the weekends.
Salem Witch Trials Memorial was the part of Salem that I enjoyed the most. It is free of charge. You will find a cemetery with a special section made with 3 handmade granite walls. The names of the 20 victims are along the walls. There are benches where you can sit in the quiet. There’s a little house you can walk through as well.
Waterfront District is within walking distance of the Witch Trials Memorial. It brings you to the coast where you can walk along a jetty to Derby Wharf Light Station built in 1871. It’s a small little lighthouse, but it has a beautiful view.
While Salem was interesting, and I felt we couldn’t leave it out when we were visiting Boston in October, it was my least favorite part of the trip. There are a lot of other places I would rather visit in the area, but I’m glad we went to check it out. Now we know what it’s about and that we will hunt for other adventures next time.
A note from our guide, Brent: “There are a number of good walking tours you can take (check out TripAdvisor). If you want to extend the day with a relaxing ride and a great view of the Atlantic coastline, we have always enjoyed taking the ferry from Salem to Boston and back. Bring a jacket!”

2:30pm Rockport, Massachussets - Cape Ann

We LOOOOVED Rockport! It’s about a 40 minute drive from Salem. It’s the most charming east coast seaside town!! We had such a good time walking down the narrow streets, looking at all the shops, exploring the stone pier, and just sitting and talking as we enjoyed the views of the harbor. We spent a couple hours here and had the best time!
We grabbed dinner on our way back to Boston at Legal Sea Foods and had some delicious soup and fresh oysters.

Day 4 Concord/Lexington, Mass - historical Sites

We started the day visiting Sleepy Hollow Cemetery in Concord. This rural cemetery is filled with famous authors and thinkers. We especially liked exploring Author’s ridge, where you will see the family plots for Ralph Waldo Emerson, Henry David Thoreau, Nathaniel Hawthorne, and Louisa May Alcott. It was a quiet and beautiful place.
Very close by is Walden Pond. Just be warned (at the time that we went) residents get in for $8, but non residents are $30. We didn’t have much time, so we didn’t do more than drive by. But I’d love to spend some time there on another visit.
Minute Man National Historic Park Massachusetts: North Bridge was incredible to see!! For me, this was the most powerful place we visited. This is where “the shot heard around the world” occurred (the beginning of the Revolutionary War and America’s fight for Freedom from England). We got to take this lovely trail and walk over the bridge. There are historical markers around the path explaining the significance and stories of the different areas. This historical park has more locations throughout Concord and Lexington. Entrance is free.
We were able to stop by Louisa May Alcott’s house in Concord, but didn’t have time to go in. I was very disappointed we didn’t get to go in! I love her books! She is an author most famous for Little Women, but Little Men and Under the Lilacs are my two favorites by her!! I will definitely be going there on our next visit.
We loved stopping by the Church of Jesus Christ of Latter-day Saints Boston Temple in Belmont. It’s gorgeous, pristine grounds are an ideal place for a quiet, peaceful moment.
ANOTHER AMAZING RESTAURENT REC!!!! We loved eating at Tatte Bakery & Cafe in Boston on our way to the airport. Everything there was a feast for the eyes as well as for the palette. WOW - is all I can say!!!

Wish List From Brent for Next Time:

“Leaf peeping” in New Hampshire in October. Drive up through New Hampshire’s White Mountains.
Brave the steep drive up Mt. Washington, which is the tallest mountain in New England, or take a cog-wheel train. On a clear day, you can see into Canada, Maine, and Vermont.
Visit Cathedral Ledge Lookout in Bartlett, New Hampshire. Drive to the top of a 700-foot granite cliff overlooking the Saco River Valley and the White Mountains. It also overlooks nearby Echo Lake State Park, which has some nice (and easy) hiking trails.

Fun Ideas When Traveling with Kids:

When we went to Boston, we went on a couples trip, but we are dying to go back with our whole family. Here are some of the things we want to do with our kids:

Read Make Way for Ducklings (children's picture book written and illustrated by Robert McCloskey ). It’s about some ducks and their ducklings who live on an island in the lagoon in the Boston Public Garden and have adventures all over Boston. You can go see bronze statues of the ducks and even take a swan boat ride.

Make Way for Ducklings 75th Anniversary Edition

By McCloskey, Robert

Boston Tea Party Museum - Re-enact the Boston Tea Party with live actors, interactive exhibits, and full-scale replica 18th-century sailing vessels!