I’ve been traveling a lot lately and last weekend I was finally able to embrace fall in Boston. Fall is my favorite season and the crisp bright sunny days are perfect to enjoy this walkable city. While out and about last weekend I noticed that many of the people I passed on the street were tourists, presumably here for some New England leaf peeping before the harsh winter sets in.
One of my favorite things to do when visiting a new city is to take a break from the textbook touristy stuff. I like to check out some places and events that locals love, so I thought I would come up with local’s guide to Boston.
Boston is a fun, young, vibrant city full of life and culture. On any given day you can find things to do. One of the best things about Boston is that if you’re not familiar with the city, you can still be in the know. When I’m looking for something to do in Boston, I check out Eventbrite, a website that gives you information and access to some of Boston’s best events and allows you to create your own.
I’m a big lover of small businesses so first on the agenda for a day in Boston would be breakfast or brunch at the South End Buttery. One of my favorite brunch spots, the South End Buttery is nestled on a cobblestoned corner in Boston’s South End. I ate New Year’s Day brunch here last year and my world has been changed ever since.
If you’re up for a walk, take a stroll from the South End to Copley Square, through Boston’s beautiful Public Garden and the Boston Common. The country’s oldest public gardens are immaculately kept, year round, and a great spot for taking pictures and enjoying the outdoors.
Continue your walk through Government Center to Haymarket where you’ll find the Boston Public Market. The year-round public farmer’s market opened just this summer and is host to dozens of local small business. Here you’ll find everything from locally sourced honey and bath products to fresh produce and baked goods.

Photo credit: Pat Greenhouse/Boston Globe
From there head to the North End, Boston’s “Little Italy” and the most historic neighborhood in Boston. It’s where Paul Revere lived (you can visit his house) and made his famous Midnight Ride warning the colonists of the British Invasion. Check out the Old North Church, the site of the lanterns that alerted Mr. Revere to the incoming Red Coats and take a tour of the historic site. I recommend touring the creepy yet informative crypts then visiting Captain Jackson’s Chocolate Shop for something sweet.

Photo Credit: Old North Church
If you’re thirsty from all of the walking, the next obvious stop is the Harpoon Brewery and Beer Hall. Located in the Seaport, a trip to the child-friendly Harpoon Brewery and Beer Hall gives you the chance to ride the country’s oldest subway, called the “T”. There’s nothing more local to Boston than riding (and complaining about!) the T. In addition to beer, Harpoon’s serves up spelt grain pretzels made from the leftover beer grains and flights of their finest brews. If you’re into beer, you’ll appreciate that you can try Harpoon Leviathan IPA, an imperial IPA only on tap at the two Harpoon breweries. Harpoon hosts events throughout the year, so check to see what’s happening when you’re in town.
For dinner I recommend venturing over to Harvard Square to Alden & Harlow, an American family-style restaurant with an eclectic menu that boasts a “secret” burger and some of the best cocktails in the city. Walk around Harvard Square as evening falls, perhaps grabbing a cup of coffee at Crema Cafe.
If you’re up for more walking, a haunted ghost tour is the perfect evening activity in the fall. Boston Intuitive offers a Spirits of Charlestown Ghost Tour that will leave you pondering the afterlife and maybe even afraid of the dark.
From there you’re on your own to relax after a long day of enjoying some of Boston’s finest small businesses and eating your way through town!