Boston fall itinerary

Boston is the perfect size to explore on foot and has such historic charm. Here's my guide to exploring Boston like a local!

Fall in New England is quite the sight as the leaves turn. It’s a time to embrace the vibrant foliage with day and weekend trips beyond Boston’s borders. While you’re at it, why not brush up on your knowledge of American history?

Fall is a great time to visit Boston. Here are our picks for fun things to do in Boston in October and November to make the most of the season.

Weekend in Boston getaway guide with itineraries for 2 days in Boston or 3 days in Boston including what to see, eat, & do plus where to stay.

Are you planning a trip to Boston this fall? It’s incredibly beautiful during the Autumn months, and I’ve got your travel guide with the best places to go and things to do while you’re there. From shopping, restaurants, and ghost tours, this post will go over everything you need to know about visiting Boston In The Fall.

This itinerary for Boston is a local's guide to the city's best restaurants, must-see landmarks, & scenic photo opportunities in 2025!

A complete guide to enjoying Boston in the Fall, compiled by a local. Tips include what to do in September, October, and November. #boston #newengland #fallfoliage

Seeing the best of Boston in one day? Yes, it can be done! Follow this one day in Boston itinerary to find out exactly how to spend 24 hours in Boston!

Boston is the perfect starting point for leaf peeping at truly stunning destinations. While the fall foliage in Boston itself is nothing to sneeze at, you’ll want to go to the mountains or seaside towns for those breathtaking views. After living in Boston for a few years, here are the top destinations I’d recommend for a fall weekend getaway. A few are even accessible by public transport! You can find a free, interactive map at the end to help you plan your trip.

In this New England fall road trip itinerary from Boston to Portland Maine you will see the best things to do in Boston, best things to do in Vermont, best things to do in New Hampshire, best things to do in Portland Maine, and best things to do in Salem Massachusetts. This fall road trip inspo is a great place to start if you're looking for fun fall vacation ideas. It also includes restaurants, bars, and hotel suggestions for each city or state.