BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
FALL BOSTON TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE

BOSTON FALL TRAVEL GUIDE

I am so excited to partner with Allegiant again this year to go somewhere that has been on my bucket list for a while now: Boston. It was just a short, direct flight from Knoxville and such an amazing fall getaway with my husband, Justin. Allegiant airlines always has such a special way of making you feel at-home with their level of care and exceptional customer service. Everything was also very clean and sanitary, which made us feel so safe and welcomed. We had so much fun that we’re already planning our next trip back! After visiting, I can see why Boston has been acclaimed for its historical beauty, great food, things to do, and wanted to share some of that with you today. So today in my Boston Fall Travel Guide, you’ll find ideas on what to do, where to shop, where to eat and where to stay while visiting this beautiful New England town during fall! 

SHOP WHAT I PACKED
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE

WHAT TO DO, WHERE TO EAT, & STAY IN BOSTON, MA

One of my favorite things about Boston is that there is something to offer every type of vacationer. No matter the type of getaway experience you’re looking for, you’re bound to have fun and find everything you need for a perfect New England fall vacation! From amazing food, taking in the history and signs, and enjoying some shopping, riding bikes, and so much more. There are so many things to enjoy in Boston during the fall, but below are some ideas to get you started and what we did during our visit!

BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE

WHAT TO DO IN BOSTON

From dining and shopping to baseball games and more, there are so many wonderful things for couples, friends and families to do in Boston. Here are some of the best things to do in Boston in the fall.

  • Explore Freedom Trail
  • North End
  • Go to a Boston Red Sox game! We went to the Red Sox vs. Yankees game and it was so fun!
  • Visit the Boston Public Library
  • Explore Boston Public Garden and capture the foliage
  • Walk Newbury Street for shopping
  • Explore Beacon Hill and Acorn Street!
  • Shop on Newbury Street, Copley Place, and Prudential Center
  • Boston Tea Party Museum
  • Isabella Gardner Museum
  • Visit Harvard in Cambridge
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE

WHERE TO EAT IN BOSTON

Y’all know Justin and I love to find the best places to eat whenever we travel to a new city. And Boston did not disappoint! Every meal we had was absolutely delicious. Below are some of the best places to eat in Boston that you should definitely try during your stay!

  • Tatte Bakery (our first stop off the plane!
  • Saltie Girl
  • Trattoria Il Panino
  • Antico Forno
  • Bagelsaurus (order ahead!)
  • Neptune’s
  • Union Oyster House
  • Mike’s Pastry
  • Modern Pastry
  • Cheer’s Bar
  • Coppa
  • Stephanie’s on Newbury
  • Sweet Green
  • Loco Taqueria
  • Lolita Taqueria
  • James Hook Company
  • Really any Italian spot in the North end!
  • Bell in Hand for drinks
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE

WHERE TO STAY

Boston has a ton of great hotel options! Boston is a small city that’s very walkable so it will be easy to explore much of the city if you’re staying at least a few days. While there’s so many that are great, my biggest recommendation is to stay close to the areas you want to explore most. The Back Bay area is a great area to stay in as it’s essentially in the middle of everything! It’s close to shopping, great restaurants. and you can easily explore other neighborhoods that are in walking distance. Back Bay is essentially in the “middle of it all,” which makes it a convenient area to stay in.

If you’ll be visiting Boston with kids, older family members, and/or plan to explore places like the Boston Aquarium, Faneuil Hall, Quincy Market, the North End, etc. you might be better off staying near the Financial District, the North End, or the Waterfront area. Like I said above though, Boston is a small city that can easily be explored no matter where you decide to stay!

WHAT TO PACK FOR BOSTON IN THE FALL - BOSTON FALL PACKING GUIDE - MUSINGS BY MADISON

what to wear in boston in the fall

And of course, if you are wondering what to wear in Boston in the fall – I have you covered there as well! The weather in Boston in late September/ear.ly October can still be fairly warm during the day, but cooler at night. So layering pieces and light jackets like this trench coat came in handy! It was a little rainy too, so I was happy I packed this plaid umbrella at last minute. Also, like I mentioned above, Boston is a very walkable city, so you’ll want to pack some comfy shoes like these sneakers for exploring. Shop everything I wore and packed for Boston in the fall below. But don’t forget, Boston has AMAZING shopping, so you can always pick up a few things while you’re there like I did!

BOSTON FALL PACKING GUIDE

more FROM BOSTON IN THE FALL

BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
ROUVALIS FLOWERS & GARDEN - BEACON HILL
BOSTON FALL TRAVEL GUIDE | MUSINGS BY MADISON, A TRAVEL BLOG BY MADISON CLEVENSTINE
HARVARD BOOK STORE - CAMBRIDGE

BOSTON FALL TRAVEL GUIDE

So, will you be making your way to Boston or New England to visit soon? I highly recommend it and be sure to bookmark my Boston Fall Travel Guide to make exploring a breeze! Xo

Thank you Allegiant for sponsoring this post and hosting our stay.

Musings by Madison is a lifestyle blog written by Madison Clevenstine. Dedicated to classic style, beauty, home decor, and travel. Rooted in passion for inspiring and encouraging others to create a home, life, + closet they love. For more content, visit my shop page or connect with me on social!