Boston, Massachusetts: Your Fall Guide

Leaf hunters love heading here in the fall, and it’s no surprise why – the beautiful white churches and classic brick brownstones juxtaposed to the vibrant reds and yellows of turning leaves are a photographer’s dream. Growing up in New England, I was completely spoiled, especially going to college in Boston, where I was at the epicenter of fall’s finest with an abundance to do. So with that in mind, I promise to provide some highlights to set you up with an absolutely perfect long autumn weekend in Boston. Pack your cable knits, riding boots, grab a hot tea or cocoa, and let’s explore New England!

Boston is a city with incredible energy, history, and rich charm. It’s surrounded by 50+ college campuses and has a youthful vibe that turns this place into a small town. Plus, lucky for you, it’s incredibly easy to get around. Boston is a great walking city – you could probably walk it in two to three hours, so it’s perfect for peeping the leaves and enjoying that crisp fall air. But, if you’d prefer to take public transportation, the T (as it’s called) is really easy to navigate and can easily toggle you between Boston, Cambridge, and Somerville. As a tourist, it’s worth getting either a weekly pass for $19 (depending on your length of stay), or a Charlie Card that you can max out or add money to in order to avoid buying single-ride tickets.

Green Line T Train

Boston – Food

Boston isn’t well-known for being a foodie town, but nestled in a few neighborhoods you’ll find some great fare. Start with the South End – while you’ll have to walk there (the T doesn’t extend that way), it’s quaint with some incredible restaurants like The Beehive (jazz brunch anyone?), South End Buttery (amazing pancakes), Flour Bakery (cookies!) and Picco for artisan pizza. However, when you say pizza in Boston, Regina Pizzeria or Santarpios truly take the cake – but these last two favorites are located in the North End and East Boston respectively.

I never thought of Boston as a food town until I started writing this blog post. The North End, apart from being home to Regina Pizzeria, is the traditionally Italian enclave that boasts some of the best restaurants around, with Limoncello as my personal favorite. After dinner, you must get a cannoli or pastry from Mike’s Pastry on Hanover Street. You’ll know it by the lines extending out the door, but they move very quickly in this Boston staple.

Boston – Fitness

If you want to work off the food from the night before, I used to love running along the esplanade. Start at the BU bridge and run along the famed dirty water of the Charles River toward the Longfellow Bridge. It’s a beautiful route, especially when all the fall colors are on display. The Head of the Charles Regatta happens in October, so if you’re around, you might be able to spot a few crew teams practicing or sail boats out for their final few sails before winter sets in.

Back Bay and Commonwealth Avenue

In Boston’s Back Bay neighborhood is Fenway Park. This baseball temple may not always have the Red Sox playing (we wish!), but tours are available. As one of the oldest ballparks in America, even Yankee fans would agree (and I grew up in Yankee country) that Fenway is worth seeing. After leaving Fenway, I would head straight into Kenmore Square, the site of the famed Citgo sign, and warm up with a famous cocktail at Eastern Standard – the bartenders are super friendly and will recommend a drink based on your personal taste. Upon leaving, there are two excellent choices. A) If you get stuck with an unfortunate rainy day, take the E train from Kenmore Square out to the Isabella Gardner Museum. The collection is superb and countless young ladies dream of getting married in the courtyard (unfortunately, ceremonies aren’t allowed). You could easily spend a few beautiful hours getting lost here and not regret a single minute.

Kenmore Square

If museums aren’t your thing, choice B is to walk down Commonwealth Avenue toward the Public Gardens and the Boston Common. I’ve walked down “Comm Ave” many times during many seasons, and between the brick brownstones, bronze statues, the yellow leaves above and crunchy ones underneath, this walk is quintessential New England.

Historic Boston

If you like history, you’re in luck. A stone’s throw from the Boston Commons leaves you smack dab in the middle of the Freedom Trail, where you’ll often spot a man sporting colonial garb leading tourists down a red brick line through many of the streets. While I’ve never done the tour, I’ve certainly gone to bits and pieces of the trail on my own to take in its history. For example, right near the Park Street T stop, there’s the Granary Burying Ground where Paul Revere, Sam Adams, John Hancock and Crispus Attucks are all buried. Walking through takes only half an hour, but you feel the weight of the history of the city and the American Revolution all at once. Additionally, and equally close by, it’s worth visiting Paul Revere’s House and the Old South Meeting House among many others to complete your historical journey of a city so rich in American History.

When we talk about Boston, it’s impossible to leave restaurants and bars out of the conversation. The oldest restaurant also happens to be the oldest in the continental United States – the Union Oyster House. While oysters are not really my thing, their seafood menu is comprehensive and outstanding. Nearby is the oldest pub in the US, the Bell in Hand Tavern. Serving normal pub fare by day, this pub turns into a bar/club by night. The lines to enter can get long in the evening, so if dancing isn’t your scene, skip the cover charge and come early for a pint.

Boston Shopping

If you prefer to shop (and don’t we all?), there’s plenty to peruse in Boston. Newbury Street is Boston’s famous shopping drag, though Charles Street in Beacon Hill is becoming a shopping destination in its own right, with adorable boutiques versus the chains and high-end brands of Newbury. Depending on the weather, Copley Square and the Prudential Center (Pru for short) have indoor shopping that will help warm up your hands and feet.

Night Sights

Rose Kennedy Rose Garden

One of Boston’s most expensive and unique hotels is the Liberty Hotel. This old prison commands a pretty penny for an overnight stay, but grabbing a drink at the Liberty Bar is a must – if not for the drinks, then definitely to see the décor.

One of my favorite places at night is the Rose Kennedy Rose Garden in Christopher Columbus Waterfront Park. With archways lit in thousands of blue lights along the waterfront, an after dinner stroll is magical, just make sure your iPhone is charged (or don’t forget your camera).

Cambridge and Somerville

A short T ride away is Cambridge and Somerville. Harvard Square is one of my favorite places with that same youthful energy encapsulated in Boston. Harvard’s campus is gorgeous, and there are many fall beer and cider festivals in the area. While in Cambridge, stop at Mr. Bartley’s, a famed small burger joint known for its hearty burgers and delicious shakes. Come hungry, but keep in mind, this tiny establishment does not have a restroom. I love exploring this area, and again, if you like history the Longfellow House is open for tours free of charge. I could spend all morning or afternoon in Harvard Square and would recommend the same.

A little further down the T’s Red Line is Somerville, which has exploded in the last 10 years. Davis Square is filled with indie shops, cafes, and the popular Anna’s Tacqueria for a quick, cheap bite. However, my favorite breakfast/lunch spot is the Neighborhood Restaurant. While they are better known for breakfast, their lunch menu doesn’t disappoint, but this delicious and inexpensive jewel closes at 4 p.m. Somerville is worth coming for lunch and staying for dinner. For a really fun late night bar and restaurant, check out Trina’s Starlite Lounge for a retro vibe and delicious craft cocktails. The T closes between midnight and 1 a.m. (it’s a major Boston flaw), but your wallet will thank you later if you catch the last T back into Beantown.

State House

While I’ve only just given you a flavor of Boston and its suburbs, what you’ll find is fun, hospitality, and safety. As a solo traveler, I’ve always felt safe in Boston and Portland (even if you’re wearing a Yankee cap). The history and culture is worth a look and a much deeper dive if you have the time. If you do make it to New England this fall, I’d love to hear about your adventures. Happy traveling!

About the author:


Sara got bit by the travel bug during her time completing a semester abroad in London, England – the most rewarding and eye-opening semester of her life. Being able to immerse yourself in other cultures and customs is what drives Sara to see the world – even though she would readily admit that she has barely scratched the surface. After graduating college, Sara took a job at a large consulting firm where she traveled weekly, amassing miles and hotel points that enable most of her travels today. Sara is never happy unless she’s planning travel; literally she loves a spreadsheet, and is looking forward to trips to Iceland, Thailand, and Turks and Caicos in early 2016. You can follow her adventures on Instagram @appetite4travel and on her blog

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