As the holiday season approaches, there’s no better time to celebrate and support the small businesses that keep our communities unique. This year, Small Business Saturday falls on November 29th—a nationwide reminder to shift our holiday spending toward local shops, restaurants, and makers. Every purchase made close to home strengthens our town centers, supports our neighbors, and helps ensure our local business districts continue to thrive. And the celebration doesn’t stop there: over the next two weeks, local merchants and community groups are rolling out festive events, special promotions, and family-friendly activities to kick off the season. Take a look at the holiday happenings around town using the links below!
Acton – The West Acton Village Stroll takes place on Saturday December 6th. Join the fun from 12:30- 4:30pm – complete the Scavenger Hunt, meet Santa and Mrs Claus, and check out the craft fair and hot chocolate station! Culminating in the tree lighting ceremony at 4:30pm. Stop by the Barrett Sotheby’s International Realty office for cookies with Frosty the Snowman!
Bedford – Kick off the holidays with a Winter Walkabout on Saturday, December 6th, with a holiday artisan’s market and open houses at local businesses. Head to our Bedford office from 3-5pm. to admire the decorated Gingerbread Village and grab a photo with Santa before he lights up the Town Common tree at 5:30pm.
Concord – The Concord Museum Holiday House Tour takes place on Saturday, December 6th - visit six homes beautifully decorated for the season. You can also enjoy holiday shopping plus festive music at the Jingle and Mingle in Concord Center that day. Be sure to return on Sunday (December 7th) for the Annual Tree Lighting and Holiday Parade from 3 - 6pm, with music, food, festivities and photos with Santa and Mrs.Claus. Don’t forget to stop by our office for some of our famous cookies! The West Concord Holiday Stroll is the following Saturday, December 13th, with visits from Santa and the Grinch and carols from the Concord Players to enjoy while you shop!
Lexington – Festivities begin from 6-9pm on Friday, November 28th with the Annual Tree Lighting in Depot Square – Santa will be there from 6:30pm, with hot chocolate, cookies and live music! Then on Thursday, December 4th get ready to shop, dine and love local restaurants and stores at the Taste of Lexington from 5 - 9:30pm
Lincoln – Join the community of First Parish Church for their annual Touch of Christmas Fair on Saturday, December 6th from 10am – 1pm. Homemade holiday crafts, wreaths, jewelry, antiques and more – plus an appearance from Santa!
Westford – Celebrate the start of the holiday season at the Annual Holiday Tree Lighting – head to Westford Town Common on Sunday, November 30th from 4pm – 5:30pm to meet Santa, hear the Westford Girl Scout Choir, enjoy crafts and games, and see the tree lit up for the season.
Winchester – The 5th Annual Holiday Stroll runs from Monday, December 1st thru Sunday, December 7th, with a host of events including Midnight-ish Madness, Red Ticket Raffle, a scavenger hunt, horse and carriage rides, and a visit with Santa. You can also vote for your favorite Gingerbread House displayed in local businesses. And don’t miss the tree lighting on the common on Friday, December 5th.