Family Fall Break – Boston Guide

I’ve decided that when it comes to a family trip/vacation over fall break , I prefer traveling somewhere cool, where it’s guaranteed to feel like fall. It’s still warm in October in Nashville, and I’m craving cooler tips and my fall wardrobe- ha! For similar reasons, I decided I enjoy visiting somewhere warm over spring break in March, as it’s still cold in Nashville that time of year, and I’m ready for warmer temps. This realization has helped me hone-in on what we’re looking for (or really, what I’m looking for) when it comes to a fall and spring vacation for the family.

I’m also interested in incorporating learning experiences into a few of our trips (aka, not all chilling at a resort or sitting my a beach the whole time), now that my kids are older. With these two factors in mind, I landed on Boston, MA as our destination of choice for fall break. Our kids haven’t been to New England, and there is plenty to see and do there as we enjoy “fall vibes” that are in full-force up north. I should note, that we’ve spent the past two years in the Highlands/Cashiers area of North Carolina- which was fabulous and also very autumnal feeling. But since we are trying out new locations with our 11-year-old daughter and 8-year-old son, I set my sights on Boston this year. It was an easy choice as it’s chock-full of history, kid-friendly and surrounded by charming small towns where we can day-trip to see even more of the area.

For this trip, I used my travel planner to help with a few things, but I researched and booked most of the trip myself. Below is our final itinerary with some notes that include other dining options and sites to see that we didn’t include on this trip, but that came highly recommended (below the three-day itinerary). At the time of writing this blog post, I’d yet to actually take the trip, so I cannot tell you it’s all good or bad, but everything came recommended by very reliable sources. I’ll be sure to follow-up after our trip, but I wanted to share this sooner than later, as I’ve had several requests to go ahead and share. Happy travels friends!

Wednesday, October 11th

2:00pm                     Arrive in Boston (pick-up rental car)

3:00pm                     Check-in The Langham Boston (250 Frankilin Street)

6:15pm                     Dinner at Banks Fish House (406 Stuart Street) *Reservation

Thursday, October 12th

8:30am                      Breakfast at Tatte Bakery & Cafe (201 Washington Street) *No Reservation- walk-in

10:00am                   Duck Tour – Departs from New England Aquarium – 80 minutes total *Reservation

11:30am                   Duck Tour ends- Walk to lunch

12:00pm                   Lunch at State Street Provisions (255 State Street) *Reservation

1:30pm                     New England Aquarium Tour (1 Central Wharf) *Reservation

4:00pm                     Tour of Fenway Park- Meet at Gate D Ticket Booth located on Jersey Street *Reservation

5:30pm                     Fenway Park Tour Ends- Walk to dinner

6:30pm                     Dinner at Stephanie’s on Newbury (190 Newbury Street) *Reservation

Friday, October 13th

10:00am                   Private Historical Tour Begins: Pick-up from the Langham


3-Hour Walking/Driving Tour of Boston:

  • Drive to Boston Common and park nearby
  • Walk along parts of the Freedom Trail and into the Granary Burial Ground
  • Pick up the car and drive the remainder of the Freedom Trail… There’s not time to go into Old North Church or Revere house, but we will pause to tell the stories of them
  • Drive to Charlestown neighborhood – Drive by the USS Constitution and walk to Bunker Hill
  • We’ll drop off here which lets the family go onto the Constitution and take their time on the ship and in the museum

2:30pm                     Head to Beacon Hill- Walk around Beacon Hill and stop in the Beacon Hill Books shop and tour/play in Boston Public Garden (duckling statue)

4:30pm                     Early Dinner at Toscano Beacon Hill (47 Charles Street) *Reservation

Saturday, October 14th

9:00am Depart hotel in rental car for Brooksby Farm in Peaboday, MA

10:00am                   Arrive at Brooksby Farm and enjoy activities on the farm (54 Felton St, Peabody, MA)

12:15pm                   Lunch at The Landing Restaurant (81 Front St. Marblehead, MA) followed by walking around town *Reservation

4:00pm                     Head back to hotel to rest and change for dinner

6:15pm                     Dinner at Figs by Todd English (42 Charles St) *Reservation

Sunday, October 15th

12:20pm                   Depart Boston for Nashville


Below are additional travel notes/recommendations from Alex (my former “everything” for Mrs. Southern Social) who lived in Boston and has amazing taste/insight!

Most of what I have here is in the Beacon Hill, Back Bay, Copley Square, and South End neighborhoods. Classic Boston. A few things to keep in mind:

  • The metro system in Boston (they call it “the T”) is very easy. Of all the places I’ve lived, I think it’s by far the most user-friendly and it’s also not enormous, so the maps are intuitive. You’ll probably be using mostly the Green line and maybe the Red if you go to Cambridge. 
  • Boston is extremely walkable, so definitely be prepared to get your steps in. Some areas can also be quite hilly (Beacon Hill) so don’t try to spend all day in a heeled boot, for example. 
  • New England is definitely more casual than the south, so don’t worry about bringing lots of special outfits for dinner. You most likely won’t have to change for most places you go. 
  • You probably already know this but just in case: the Charles River divides Boston from Cambridge. You’re staying on the Boston side, but Cambridge is literally just across the bridge. AKA, not far away. 

To Do (for you):

  • Isabella Stewart Gardner Museum (I interned here one summer in college! Love this little museum) 
  • MFA – there are some great exhibits coming up like this Sargent one.
    • Note: the museums are next to each other, so it’s easy to hit both at once. If you’re up for it, it’s actually a nice walk on a nice day from the center of town (Back Bay area) to the museums. You can also hop on the Green Line (use the E train) and get off at the MFA stop. 
  • Beacon Hill Books & Cafe 
    • Note: You will die for Beacon Hill. It’s an old, super charming part of the city that still feels very “original.” It’s darling and you will enjoy poking around the main drag, Charles Street, and wandering up all the hills to see the pretty houses. Louisburg Square is not to be missed – just trust me. Louisa May Alcott owned a home there. Beacon Hill is right behind the State House, which was built on property that used to belong to John Hancock. Here’s more info.
  • The Esplanade is the river-front pathway and parks along the Charles on the Boston side of the river. Ideal for walking, running, and letting the kids play. You can also walk across the bridges to Cambridge and there is a riverside path there as well. There are playgrounds and boat rentals and really beautiful views, and in October the foliage will be great. 
  • An interesting thing to do that’s “cultural” but relatively quick is the art and architecture tour at the Boston Public LIbrary, which is a stunning building in Copley Square. McKim was one of the architects and it has big pieces by Sargent.
    • Copley Square (named for the artist) is really beautiful and you’ll recognize it because it’s one of the iconic “views” in Boston. It’s used in b-roll footage whenever a movie or TV show needs to tell the audience “this is set in Boston.” Trinity Church is gorgeous and worth a peek inside – here’s some context
  • The Harvard Art Museums are wonderful – there are three right next to each other: the Fogg, the Sackler, and the Busch-Reisinger. It’s a nice walk over to Cambridge from Boston. 
  • The famous Head of the Charles Regatta is Oct. 21-22 this year – if your visit overlaps, it’s definitely worth watching some of it. 

To Do (for kiddos):

  • Freedom Trail
  • Boston Children’s Museum (not sure if G is too old? I don’t think so but check) 
  • Fenway Park Tours  (I’ve not done a tour but if you can’t go to a game – you’re there too late I think – you’ve got to at least see the stadium. It’s so iconic.)
  • Aquarium
  • Sadly, when you’re there in October, the Swan Boats in the Public Garden will already be closed for the season. But the Public Garden and adjoining Boston Common are beautiful green parks and they’re perfect for a picnic. You can get charcuterie for your picnic from Formaggio in the South End or Savenor’s in Beacon Hill. Fun fact: Savenor’s was Julia Child’s go-to market. 
  • I know your kids are too old but you’ve got to see the famous “Make Way For Ducklings” sculpture in the Public Garden. The book is of course set there.


Admittedly, not all of these are necessarily kid-friendly – remember, we lived there in our early 20s! Ha! I put an asterisk next to options that I think are especially kid-friendly, but your kids are older and well behaved, so I really don’t think there are many places you couldn’t take them. I also always trust the Eater guides (just keep in mind that this includes restaurants in the greater Boston area, as well – aka, not around the corner).

Lots of the restaurants we liked are in the South End, which is an area south of Copley Square. It’s full of charming cobblestone streets and is lovely to wander around, though it’s not where you’ll find the main historical sites/museums. It’s more neighborhood-y. It’s an easy cab ride from your hotel (or about a 30 min walk). 

The North End is like Boston’s Little Italy and I think that area would be really fun for G and JA. It’s also close to where you’re staying. Admittedly I’m NOT an expert on those restaurants so I’d ask your concierge for some ideas. We did go to Giacomo’s several times when I was living there and the reviews still look good, so I included it on this list. 

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