A confession: I secretly take credit for Small Business Saturday.
I’ve been sourcing as many Christmas gifts as I can from local stores for over 20 years. I used to make it my special day: head to those cool little shops where not only can you find something special for your gift, but you almost always get to meet the shop owner too. It’s great and I wouldn’t have it any other way. I had to be the one who started it all, right?
I’m not totally wrong, because Small Business Saturday was created by all Bay Staters. In 2010, Boston Mayor Thomas Menino, in partnership with American Express, the National Trust for Historic Preservation, and Roslindale Village Main Street formally launched what is now an annual event celebrated in all 50 states.
This year, Small Business Saturday takes place on November 30 (the day after Black Friday and the Saturday before Cyber Monday, as is tradition). If you haven’t committed to buying local for the holidays before, give it a try this year. And even if you only do some of your shopping that way, you’ll come out a winner, as you’ve helped local businesses thrive and treated yourself to a beautiful day in one of the Bay State’s fun, cozy little town centers.
Consider these for your Small Business Saturday:
Cityscape – Roslindale Square: Where it all began and where you can still enjoy a classic downtown neighborhood, savor good food, and yes, find gifts that definitely won’t be fooled.
Roslindale (https://www.roslindale.net) is scenic, walkable, and has excellent parking. You can spend a full day as the neighborhood goes all-in on the holidays with “Small Shop Bingo,” a game you play while you shop and where you can win big prizes and local music performances on the street and indoors. and dance groups, and at dusk, the lighting of a tree with the participation of Boston Mayor Michelle Wu.
They even published a gift guide to help you plan your adventures and purchases.
North Boston – Newburyport: Newburyport is a city worth visiting any day. The crystal-clear water, classic New England architecture, incredible dining spots, and many unique shops make this destination worth a visit.
The city center is beautiful, picturesque and fun.
Small Business Saturday means the more than 150 shops and restaurants that line the city’s waterfront area will be offering special discounts and special experiences.
Arrive early, park your car, and let the day unfold—you can recharge at Buttermilk Baking Company and then let your feet guide you. The city’s waterfront walking and biking trail, the Clipper City Rail Trail, is worth a trip and will take you to different shopping spots as well as some historic signs that will familiarize you with the area.
To be prepared, you can download an application that guides you to everything you want and need in https://newburyport.com. Best advice? Make it a full day, including dinner.
There are other great options north of Boston like Rockport, Ipswich, and Salem. You can choose one or mix and match them for a perfect shopping trip.
Down on the Cape: Cape towns are known for salt air, clam shacks and lighthouses, but there are also great places for days of shopping. On Small Business Saturday, consider spending a day along Hyannis’ Main Street, where you’ll find locally owned shops, great food, and plenty of history to take in as you go. Arrive and park for the day (as a resort town, it has plenty of spots) and then walk to Main and back, visiting clothing boutiques, art galleries, shops with creative goods, and more.
Continue walking through the shopping area towards the ferries for a fun look at the artist shacks along the boardwalk, as well as a beautiful walking trail.
You’ll also find a perfect park and all-day shopping scene in Chatham, and of course, beloved Provincetown, as always, offers shopping deals, a festive atmosphere, and lots of fun.
Bonus: Little to no traffic on the bridge this time of year makes the round trip easy. You can find all kinds of information at https://www.capecodchamber.org.
And although it’s not on the Cape, downtown Plymouth, with blocks and blocks of locally-operated shops and restaurants, is a quick hop from the highway and worth a full day in itself. More about what it has to offer at https://seeplymouth.com
