Sidewalk Sales
Many local merchants mark down their prices, bringing fabulous finds out onto the sidewalks, where you can browse in the sunshine and snag a bargain or two. We did a little hunting ourselves and uncovered some of the best summer sidewalk sales in and around Boston—and we’re excited to share our finds with you.
Remember: Bargains are out there... you just have to step outside and go find them! Over the years, we’ve discovered some of the top spots for sidewalk sales in Greater Boston, including:
Newbury Street “Open Newbury” Street-Sundays
Occurring every Sunday through August 25, including Aug 4, 11, 18, and 25.
Newbury Street will close to traffic, creating a vibrant outdoor shopping atmosphere with sidewalk sales, patio dining, and live music into early evening.
Great for exploring all the new additions to the area.
South End Sidewalk Sale
Traditionally takes place in late August (often in conjunction with South End Feast or HONK! Festival).
Features dozens of boutiques setting up deals right on the sidewalks
Wellesley Square Summer Sidewalk Sale
Known for upscale markdowns from independent retailers. (USUALLY held in JULY – BUT MAY ADD AUGUST, KEEP YOUR EYES OPEN)
🛍️ More Sidewalk Sale Events
Sudbury Summer Sidewalk Sale (Route 20 Corridor)
Many shops along Route 20 routinely hold mid-summer sidewalk sales in late July and early August. Keep an eye on local retailers like antique stores, boutiques, and gift shops—they often display banners or set out tables on sidewalks.
Hudson (20 min away)
Downtown Hudson hosts a Saturday "Sip & Shop" street series, often with adjacent merchants offering sidewalk markdowns throughout July and August . While not a dedicated sale, the mix of live music and outdoor shopping creates a festive vibe similar to a sidewalk sale.
Cambridge
Cambridge Plays (May 16 – August 31, 2025)
Step Outside and Join the Fun!
As the warm weather rolls in, the Community Development Department (CDD) teams up with local businesses and organizations to bring free, family-friendly events to parks, plazas, and public spaces throughout Cambridge.
Cambridge Plays is all about:
Inspiring people to enjoy the city’s vibrant commercial districts and public spaces
Bringing neighbors together and expanding access to arts and cultural experiences
Creating inclusive, welcoming spaces that actively promote anti-racism
Supporting the city’s amazing small businesses
Honoring and celebrating the rich cultural diversity of Cambridge
Hosted by the city’s Community Development Dept, this program invites local businesses and organizations to host cultural and commercial events on sidewalks and plazas throughout Cambridge’s commercial districts
Think pop-ups, sales, demos, small workshops, performances—it’s broad and community-focused.
If you’re a business, you can still apply for events happening through the end of August. General public: keep an eye on local business districts (like Harvard Square, Inman Square) for surprise happenings!
🌉 Somerville
While there's no official “sidewalk sale” listed for 2025, Somerville’s SomerStreets (annual open-streets festival) often turns commercial strips (like Highland Avenue) into pedestrian-friendly zones with vendor stalls, food, crafts, and sometimes sales—though it’s more of a block party than traditional sidewalk sales somervillema.gov.
🏖️ Winthrop
No upcoming planned sidewalk or town-wide garage/yard sales flagged for August or summer 2025 on the town calendar
Residents often host informal yard sales (see local FB community posts), but nothing formalized as a sidewalk sale event for this summer .
And Devon would like us to remind you....Some sidewalk sales happen in early summer too. Has your town already had theirs? Or, is it coming soon? Do you go? We suggest you give it a try. Some of the best bargains and real steals we have ever gotten were found at a sidewalk sale.
Check this out, our writer Renee got a “fantastic painting,” still in her home, for five dollars. And one of our staff found some gorgeous earrings for four dollars. That was four years ago, and she still wears them! Sidewalk Sales, here we come!