Boston By Squares: Eat + Shop Locally

There are so many ways to shop for gifts this holiday season. Of course there are the big culture killing, small business brutalizing, overpackaged mammoth companies or you can shop local. Shopping local does not have to be complicated either. You can spend one day at a holiday market, or if that is an overwhelming prospect, head to a local square grab a coffee, lunch or dinner in the neighbhourhood and start checking people off your list.

If all of that doesn’t work, there is always the option to shop online locally too. I like to go onto Etsy and filter to my state or city so I can shop locally that way. My sweet spot for shopping is to take a stroll in a neighbourhood, maybe meet someone for coffee or dinner mid-way through and make a 1/2 day of it.

Boston the City of Squares but No Right Angles

I learned very early on that Boston and surrounding areas have many squares that are not exactly squares. They are basically little neighbourhoods with restaurants and shops and are basically any shape but square and are rarely around a square intersection either.

Squares to Shop Small

Cambridge + Somerville: Camberville

Davis Square: On the Red Line, plenty of places to enjoy food and drinks and shop. Mostly independent boutiques and stores.
Energy: lots of students given how close it is to Tufts, a slight bit of grunge and lots of hipster energy
Instagram accounts to follow: @SomervilleFlea, @SomervilleArtsCouncil,
T Stop: Davis

Harvard Square: On the Red Line, plenty of places to enjoy a drink or a nibble and shop. A mix of trendy chain stores and independent boutiques.
Instagram accounts to follow: @CambridgeUSA, @Harvardsquare,
T Stop: Harvard

Porter Square: On the Red Line, quite a few places to enjoy a drink or bite to eat, many casual options as well as some fancier spots on the walk from Porter to Harvard Sq.
Instagram accounts to follow: @Porter_Square_Books, @Cafe_Zing, @MommasCambridge
T Stop: Porter

Inman Square: Inman Square doesn’t have an easy T stop and is definitely smaller than the others but totally worth it just for Albertine Press and Gather Here. I would do Harvard Square or Central Square and then walk over to Inman Square or start in Inman Square and then head over to Harvard or Central Square for a bite to eat before continuing on shopping.
Instagram accounts to follow: @GatherHere, @eastcambbiz

Boston

South End (Harriet Tubman Square, Blackstone Square, Franklin Square, Chester Square): A bit more spread out, but there are some great options for dining and shopping. Mostly artists studios and higher end boutiques with some of my favourite shops that have a nice range of gifts and various prices.
Instagram accounts to follow: @SouthEndBusiness, @SowaBoston, @SOWAArtistsguild, @InkBlockBoston
T Stop: Back Bay

Beacon Hill (Louisburg Sq): Charles Street is my favourite shopping strip and I like to grab a little drink and bite to eat along the way too. I would do Charles Street and then head to Newbury Street to get a good amount of shopping done. Beacon Hill is mostly small boutiques and a few little local chains as well.
Instagram accounts to follow: @beaconhillbooksandcafe, @historicbeaconhill, @bucketlistboston, @savor_roam
T Stop: Charles/MGH

Jamaica Plain (Monument Sq): Jamaica Plain has the pond which is a perfect little walk all four seasons (for a true New Englander) and a nice little strip of indie shops and places to get a meal or snack along Center Street. Instagram accounts to follow: @jamaicapond, @onsjamaicaplain, @houseofwoodbourne
T Stop: Green Street Station

Chinatown (Phillips Sq Plaza): Okay so Phillips Sq plaza is the most un-square square but it is officially in Chinatown and if anyone wants to find a real square in Chinatown it would of course have to be the plaza by the Chinatown Gate, but I have a theme so I’m sticking with it. Chinatown has so much good food in a small radius, but there are also plenty of little shops for everything from little trinkets to teas and housewares. I like to just zig zag my way through Chinatown and pop into places, but you can also check out this very comprehensive map of what to find where.
Instagram accounts to follow: @jccraves, @fanchinatown, @chinatownmainstreet, @onschinatown
T Stop: Chinatown

Allston/Brighton:(Oak Square): So the newer things are the Landings (Boston Landing) and the Yards (Allston Yards). Then there are old things made new again Speedway (Charles River Speedway) and just the old corners (Packard’s Corner). Allston/Brighton is not on the T but with the new Boston Landing station you can take the commuter rail (take advantage of those $10 weekend passes) and get to the Boston Landing end of things. I love Allston/Brighton for the food, the little extra bit of grit as you walk around, and the little almost all local shops sprinkled throughout.
Instagram accounts to follow: @allstonvillagemainstreets , @zone3westernave, @bostonlanding, @charlesriverspeedway, @brightonmainstreets, @allstonbrightonons
T Stop: Boston Landing Train Station, Harvard Ave

Dorchester (Codman Sq): Dorchester is another spot with plenty of tasty places to eat and many local indie businesses to shop. Dorchester is another area that is quite spread out and not super accessible by T but you can bus/t/walk just about anywhere or hop on a Blue Bike when the weather is nice. You may also be able to take advantage of the $10 commuter rail weekend pass and use that to get where you want to go in the neighborhood.
Instagram accounts to follow: @dorchesterons, @greaterashmont, @fieldscorner

A Few Folks Worth a Follow

General Instagram accounts to follow for all the squares and beyond. @thefoodlens, @nailthecocktail, @onlyinbos, @forkingwitharmani, @BostonMagazine @streetscapecurator, @travellikealocalma, @blackownedbos, @AlexandraMakeba, @lifeasamaven, @confessionsofachocoholic, @viviandfoodie, @cantreadthestopsigns, @AlexisAList @seansweeney2017, @heythereney, @brianmcw, @trishofthetrade, @harlemlovebirds, @scienceteacherphotos