Why you should visit Boston this autumn

BY Valentina Valentini

15th Sep 2023 Lifestyle

4 min read

Why you should visit Boston this autumn
Autumnal colours and green spaces, eating and drinking, cultural events and shopping—there are many reasons why Boston is always a great choice for a quick American getaway. So head to the New England city for a holiday this autumn
Autumnal Boston might be the best Boston. The city has that crisp New England air about it, the crowds and the heat from summer have died down, but sunny days still outnumber rainy ones; the bustle of the holiday season hasn’t started in earnest yet, and prices for airfare and accommodation are more affordable.
"Autumn foliage is one of the first reasons people think to head to New England in the autumn"
With daily non-stop flights from London Heathrow on many major carriers and lower fares on budget airline Norse Atlantic from Gatwick, Boston is one of the most accessible American cities for us. Plus, Boston has been working hard to become a world-class city by offering travellers truly prime visiting accommodations and experiences. Just look at Raffles: the iconic Asian hotel chain chose Boston as their first North American home, and the Raffles Boston Hotel is opening to much fanfare this very autumn.
And it goes without saying that autumn foliage is one of the first reasons people think to head to New England in the autumn—and you’ll get to see plenty of it if you time your trip right! This small, walkable, coastal city has so many options for tourists it’ll be hard to fit them all in.

Eat your heart out in Boston

A seafood dish from Carmelina's
Nautilus Pier 4 is a surprising and delectable culinary experience of classic New England seafood-forward, Asian-inspired dining. With views of the water, of course. Try the blue crab fried rice—it’s inspiring.
The North End is chock full of incredible Italian restaurants, so it can often be intimidating to choose. But Carmelina’s is top of our list for its menu full of fresh ingredients, classic homeland dishes mixed with modern Mediterranean plates and owner Damien Dipaola’s mother’s recipes like Sunday Macaroni and Crazy Alfredo.
High Street Place Food Hall is more than just a food hall. Though, the food on offer is varied and delicious (we like Haley Jane’s fried chicken sandwiches, extra pickle, the burgers from Wheelhouse, and the pepperoni pizza from Tenderoni’s), High Street Place has DJs Thursday to Saturday, quiz nights on Tuesdays, Workshop Wednesdays, and they’ve even got rooftop yoga on tap. If you’re in town on September 23, head over for their Fall Fest, an all-day free event with seasonal menus, pumpkin decorating, Stein-holding contests and more.

Boston brews

Head on over to Seaport District for drinks at the new Trillium Brewery for local-only craft beer that you can’t get anywhere else. They’ve got pool tables, too, and gastropub-style food.
Democracy Brewing is a worker-owned micro-brewery that opened in 2018. The vaulted ceiling transports you to something like European beer halls, but the casual atmosphere where you can smell the goodness coming out of the kitchen let's you know you’re still in Beantown, as the city is sometimes affectionately called.
"Samuel Adams Boston Brewing Co. spearheaded the craft beer revolution in New England "
Founded in 1984 by Jim Koch, the Samuel Adams Boston Brewing Company (named after one of the country’s founding fathers, Sam Adams) is a Massachusetts institution. The business spearheaded the craft beer revolution in New England when Koch first brewed the Boston Lager over 30 years ago. Now, their Fanueil Hall tap room and Jamaica Plain tap room and brewery are great spots to check out their innovations or just enjoy a cold Sam Adams.

Shop ‘til you drop

Event poster for Black Owned Bos. Market in Boston
One might not think they need a shop filled to the ceilings with jeans, but one trip to Injeanius and you will understand why it’s a must. This bespoke denim shop was opened by a local woman who aimed to take the guesswork out of picking a pair of jeans. She will help you try on as many pairs as it takes to find the right one. Or two. Or five.
In the same neighbourhood, on October 8, the Black Owned Bos. Market returns for its fourth year, with over 60 vendors at an open-air market for its “Fall Fest.” It’s a great way to support locally-owned businesses run by underrepresented groups. There will be beverages Caribbean Latin fusion food, live music and more.

The great outdoors

Bunker Hill Monument, Boston
Urban hiking is a new trend in travel, and Boston is leading the way with their Walking City Trail which debuted last summer and is comprised of pre-existing green space pathways and city walkways. Hike the whole 27 miles from the Neponset River Reservation south of city to the Bunker Hill Monument in Charlestown, or take it in chunks. Section 4 has a nice mix of cityscapes, waterways and green spaces and winds you through the central core of Boston.
England might have the most prestigious rowing competition in the world, but Boston has the biggest. There is nothing quite like experiencing the three-day regatta with 40,000 spectators along and across Boston’s Charles River, an iconic part of the city. The Head of the Charles Regatta starts on October 20, and brings with it all ages and manner of person to watch and celebrate in a thrilling feat of strength and stamina.
"The tour takes you to Boston Light, America's first lighthouse station"
Only accessible by public ferries from mid-May to mid-October, adventure out to the Boston Harbour Islands. The two-hour narrated lighthouse tour takes you to Long Island Light, Graves Light, and Boston Light, America’s first lighthouse station. There's also camping on Paddocks Island, and picnic tables on all of the islands. Make sure to pick up some Boston staples, like clam chowder or lobster rolls, at Long Wharf North or Faneuil Hall Marketplace and bring a bag to bin your waste and leave no trace!

Cultural cache

Mr Swindle’s Traveling Peculiarium mostly sticks to the southeastern United States, but for three wild weeks beginning October 12, the vintage entertainment emporium—chock full of comedy, acrobatics, and other shenanigans—will be in Boston. But you’ll have to leave the kids home for this one, it’s 18+.
"The autumn months bring with them a treasure trove of cultural events in the Greater Boston area"
The autumn months bring with them a treasure trove of cultural events in the Greater Boston area. Though it’s not an exhaustive list, here are some that we think should be top of mind if you’re visiting in September, October, or November: Indigenous People’s Day celebrations; Harvard Square Oktoberfest; Cambridge Science Festival; Boston Ballet Fall Experience; and Boston Public Market Harvest Party. They’re a mix of free and ticketed events, some family friendly and some better for adults. But whatever the celebration, we’re confident your time in Boston will be well-spent.
Banner photo: Boston skyline by Sean Pavone
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