How to Have the Perfect Fall Foliage Day in Boston

Complete with scenic views and, of course, a place to get a cider doughnut.

Photo by coleong/Getty Images

Look, there’s a reason the beloved Onion article extolling the virtues of fall in New England plunks Mr. Autumn Man down on Mass. Ave. Sure, they’re making fun of our obsession with the season…but Mr. Autumn Man would hardly be strolling around any other city “wearing a gray sweater over a plaid collared shirt as he cradled a cup of pumpkin-spiced coffee.” This time of year? This is Boston’s time to shine. And thanks to the marvel of modern science, we know exactly which weekend will be the perfect one to experience the changing colors without leaving the city. According to the interactive map published every year by smokymountains.com, the best weekend to enjoy the bright colors right here in Boston will be October 11. Armed with this knowledge, you’re ready to have a Hallmark movie-style, Onion-spoofing, so-autumn-it-hurts day in Boston. Here’s what you should do.

Get ready in advance with the proper fall fashion

You have plenty of time to prepare, so start by selecting the perfect shirt to wear on this excursion: a flannel. Your options are bountiful around New England, making it that much harder to select the right one for you. Fret no more: We have a quiz to find the right flannel for you. Take it, flannel up, select your favorite pair of long walk-appropriate footwear, and hit the road.

Power up with a breakfast sandwich

It’s important to make sure you’re energized for the day ahead. That’s why you want to grab a breakfast sandwich at the beginning of the day. If you’re a Dunkin’ or bust diner, try our ranking of their sandwiches and pick accordingly. But for a little more variety, try our list of the best breakfast sandwiches in Boston. There’s probably something deliciously savory awaiting. And look, we all know you’re stopping for one of those doughnuts later in the day, but if you also want to start your day with a nice doughnut, here’s a roundup of the city’s finest offerings.

Head up to a high point and take in some of Boston’s best views

You’re energized and you’ve got the whole day ahead of you. Time to clamber up a steep hill to see some of the city’s best views. The Bunker Hill Monument is a fine and traditional option, but don’t miss Prospect Hill if you’ve started your day in Somerville, or take in the sights from one of the bridges over the Charles River. Does the Boston skyline look awfully pretty as a backdrop to a riot of red and gold and orange color? Why yes, it does. If you’re a bit of an urbanist, you should also try this walking tour of some of the city’s coolest and most unusual architectural sights.

Find your fall read

You may be in this for the leaf peeping, but that doesn’t mean you’re not also preparing for a rainy day when you’ll huddle up under your warmest quilt, steaming mug of hot cider in hand, and read a good book. That’s why you need to head to Best of Boston winner Frugal Bookstore in Nubian Square to get something to read. Need to rejuvenate? Stop by Soleil Cafe while you’re there and grab a cup of coffee.

Take a lunch break

OK. You can pretty much go anywhere for lunch, and the point of this day is to treat yourself. But early October is one of the last times the temperature is fairly moderate around here, so layer up a second flannel shirt and try one of the best options for outdoor dining around town to keep the autumnal vibes going. These patios all offer something special, but if you’re looking lunch-specific, Bow Market has something to nosh all day, Charlie’s Kitchen gives you one of the area’s cheapest lobster rolls and a prime opportunity to wander Harvard Yard afterward, Lulu’s in Allston helps you get in a quick round of bocce, and Reelhouse in Eastie provides prime harbor views.

Peep some trees

It’s time to prioritize what we’re here for: trees. Now, obviously you can swing through Boston Common and the Public Garden for some sights, but the real prize is the Arnold Arboretum in Jamaica Plain. The park offers 281 acres of trees to explore on your own, or you can sample one of their recommended walks, all easily reached via the Forest Hills Orange Line stop. Linger as long as you like beneath the branches, take all the photos you’ll need for Instagram, and rest easy knowing Boston just does fall better. Another classic option? Walking along the Esplanade, where there are also ample opportunities for picnicking and people watching (and if you’ve pushed out your foliage day to Oct. 22, you can catch some of the Head of the Charles Regatta). Bonus activity: Stop at Georgetown Cupcake on Newbury Street, find a bench in the Garden, and then see how many wedding and engagement photoshoots you can spot.

Fuel up with a cider doughnut

You know what you’re here for: a cider doughnut. Now, if you’re willing to travel a bit, you can get these almost anywhere in New England for an Authentic Fall Experience. But since we’re staying in the city, you want to head on over to the Boston Public Market and sample some of Red Apple Farms’ finest (and if you’re heading over from Forest Hills, it’s an easy jaunt on the Orange Line to North Station. See? It was meant to be). Plus, the doughnuts are made right in front of you, and if you don’t want to stare, rapt, at a cider doughnut machine as it crafts an infinite supply of the sugary delights, then, well, why are you reading this article? But we recognize that cinnamon may not be everyone’s flavor, and suggest you indulge your sweet tooth using this roundup of local chocolatiers instead—most of them can also hook you up with a hot chocolate to take on the road, if that’s your thing.

Find a more peaceful location as the sun sets

If you’re a true autumn aficianado, you know that part of what makes the season so affecting is the embrace of feeling melancholic as the last heat of summer fades away and you brace for the oncoming winter. For your final leaf peeping of the day, go over to Mount Auburn Cemetery. Meditate about the brevity of life as you stroll among the beauty of the grounds. Or, you know, make a quest of finding all the famous people buried there.

Relax with dinner and a movie

If you wanted to go all in on this concept, you could probably pick out a restaurant based on Autumnal Vibes. Or you can just warm up after a long day outside with our guide to the city’s best mac and cheese, and give yourself a break from pumpkin everything. Once you’ve dined, take in a movie at the Brattle or the Coolidge, or head home to watch a classic Massachusetts movie—go Hocus Pocus or Session 9 for spooky viewing, or settle in with Next Stop Wonderland for a delightful ’90s era indie rom com. And if there isn’t enough spooky stuff in this list for your taste, bundle up for a night out on the haunted trolley tour and learn about some grisly happenings around town. Congrats! You are officially an Autumn Person.