🎄 Winter 2025 Holiday Markets & Special Events in Greater Boston 🎄

A STRUCTR Guide to Shopping Local All Season Long

Boston in December is peak cozy: lights in every window, snow (usually), and more holiday markets than you can reasonably hit in one weekend. To make it easy, we’ve pulled together a complete guide to this year’s holiday markets and special pop-ups across Greater Boston — all focused on local makers, artists, and small businesses. Boston Art Review

Whether you’re a renter, homeowner, or investor, these events are perfect for finding unique gifts, upgrading your space, and getting to know different neighborhoods.

🛍 Ongoing Pop-Up Markets (All-Season Staples)

These are the markets you can return to again and again throughout December. Boston Art Review

SoWa Winter Festival – South End

Through December 28 · Tues–Sun, Various times📍 SoWa Power Station, 550 Harrison Avenue, Boston, MA 02118

An indoor market inside a historic power station, featuring regional makers, designers, and specialty food. Think: craft-forward, artsy, and very “South End.” Boston Art Review

Snowport Holiday Market – Seaport

Through December 28 · Various times📍 100 Seaport Boulevard, Boston, MA 02210

Seaport’s famous winter wonderland: 100+ vendors, food and drink, twinkly lights, and plenty of photo moments. Ideal for a full outing — shop, grab a drink, and wander along the waterfront. Boston Art Review

Downtown Boston’s Holiday Market – Downtown Crossing

Through December 21 · Thu–Sat, 11am–4pm📍 10 Summer Street, Boston, MA 02110

An easy stop right in Downtown Crossing: rotating vendors, artisan goods, and seasonal treats. Great if you’re already downtown for work or errands and want to squeeze in some festive shopping.

Sudbury Art Association Holiday Market – Sudbury

Through December 23 · 10am–6pm📍 29 Hudson Road, Sudbury, MA 01776

A charming, gallery-style market featuring local art, ceramics, textiles, and handmade gifts. Perfect if you’re west of the city (or house-hunting out that way) and want to support local artists.

✨ Special Events: One-Day & Limited-Run Markets

These are the don’t-miss dates — perfect to plug into your calendar now. All of the events below come directly from Boston Art Review’s 2025 holiday markets roundup. Boston Art Review

#ShopAAPI Holiday Night Market – Back Bay

December 3 · 5–8pm📍 10 St. James Avenue, Boston, MA 02116

An evening market centering AAPI-owned businesses, with gifts, art, and design-forward goods — ideal for thoughtful, community-minded gifting.

Winter Gift Market at Sudbury Holiday Village – Sudbury

December 6 · 11am–3pm📍 Fairbank Community Center, 40 Fairbank Road, Sudbury, MA 01776

A family-friendly daytime market with local vendors and a cozy, small-town feel — great for pairing with a weekend drive.

Andover Holiday Market – Andover

December 6 · 12–6pm📍 South Church Andover, 41 Central Street, Andover, MA 01810

Featuring local artisans and food vendors in a classic New England setting — perfect if you live north of the city or are exploring new suburbs.

Christkindlmarket – German Holiday Market – Allston

December 6 · 3–7pm📍 57 Holton Street, Boston, MA 02134

A German-style holiday market with traditional food, drinks, and décor — a great option for families and anyone looking for a European holiday vibe. Boston Art Review

Boston Women’s Holiday Market – Multiple Locations

December 6, 7 & 13 · Various times📍 The Huntington Theatre (Boston), Prudential Tower (Boston), Night Shift Brewing (Everett)

Featuring women-owned brands and makers across three venues — think candles, textiles, jewelry, and cozy goods. Ideal for building gift boxes for clients, tenants, or new homeowners. Boston Art Review

Winter Fest 2025 – Charlestown

December 6 & 7, 12–14, 19–30 · Various times📍 The Yard at Hood Park, 100 Hood Park, Charlestown, MA 02129

A multi-week festival with vendors, food, and winter activities in a redeveloped industrial space — a great way to get a feel for evolving Charlestown.

Small Mart Holiday Market – Davis Square, Somerville

December 6 & 20 · 11am–4pm📍 Somerville Theatre, 55 Davis Square, Somerville, MA 02144

A fun, indie-leaning market inside Somerville Theatre, bringing together small brands and artists in the heart of Davis Square.

Somerville Flea Holiday Markets – Somerville

December 7 & 21 · 10am–4pm📍 191 Highland Avenue, Somerville, MA 02143

Vintage, records, art, and more in a creative community space — perfect if you love character-filled finds for your home or rental.

Winter Market at Sam Adams Boston Brewery – Jamaica Plain

December 7 · 12–5pm📍 30 Germania Street, Boston, MA 02130

Beer + local makers = a very JP holiday. Browse vendors while you sample seasonal brews at the original Sam Adams brewery.

Roslindale Holiday Market – Roslindale Village

December 11 · 4–8pm📍 Birch Street Plaza, Roslindale, MA 02131

An outdoor neighborhood market in Rozzie, with local creators and small businesses. Great for exploring one of Boston’s coziest village centers.

Harvard Ceramics Winter Show & Sale – Allston

December 11–14 · 10am–7pm📍 224 Western Avenue, Allston, MA 02134

Hosted by the Ceramics Program, Office for the Arts at Harvard, this show & sale is pottery heaven: mugs, bowls, sculpture, and more — perfect for elevating your kitchen shelves or staging a property. Boston Art Review

Andem Art Studios’ 5th Annual Holiday Show & Sale – Brookline

December 12–14 · Various times📍 Station Street Studios, 17 Station Street, Suite 206, Brookline, MA 02445

A studio show highlighting local artists’ work in an intimate setting — a great way to discover original art for your walls.

Harvard Square Holiday Fair – Cambridge

December 12–14 & 19–21 · Various times📍 Corner of JFK & Winthrop Streets, Cambridge, MA 02138

A long-running, high-energy craft fair with vendors from New England and beyond—pottery, jewelry, textiles, and more. A classic Cambridge holiday experience.

Canal District Winter Market – Kendall Square, Cambridge

December 13 · 11am–6pm📍 650 E Kendall Street, Cambridge, MA 02142

A waterfront-adjacent market in the growing Kendall area, showcasing local makers against a tech-district backdrop.

Cambridge Arts Holiday Art Market – Kendall Square, Cambridge

December 13 & 14 · 12–4pm📍 650 East Kendall Street, Cambridge, MA 02142

A curated art-forward market run by Cambridge Arts, featuring local artists and creative vendors — great for picking up original, giftable work.

Boston Harbor Distillery Holiday Sip & Shop – Dorchester

December 14 · 12–5pm📍 12R Ericsson Street, Boston, MA 02112

Craft spirits plus local makers in a historic distillery building on the waterfront — ideal for adults-only shopping with a side of tasting.

Small Business Holiday Pop-Up at Project Hustle – South End

December 20 & 21 · 11am–4pm📍 59 Wareham Street, Studio #5, Boston, MA 02118

A studio pop-up focused on small businesses and independent brands — another great excuse to wander the South End’s brick streets.

The Speedway Holiday Stroll – Brighton

December 20 & 21 · 12–5pm📍 The Charles River Speedway, 525 Western Avenue, Brighton, MA 02135

Part market, part neighborhood party in a redeveloped historic complex with shops, food, and outdoor gathering space.

🏠 How STRUCTR Clients Can Use This Guide

As a real estate + property services company, STRUCTR is all about helping people feel at home in Greater Boston. Here’s how you can make these markets work for you:

• Decorate with intention: Pick up ceramics, textiles, prints, and ornaments that bring warmth and personality to your home, condo, or rental.

• Level up welcome gifts: Landlords and hosts can build small, locally sourced welcome kits (mugs, coffee, candles, treats) to delight new tenants or guests.

• Scout neighborhoods: Use markets in Roslindale, Somerville, Charlestown, Brighton, and beyond as a low-stress way to experience areas you might want to live or invest in.

• Support the ecosystem you live in: Shopping from local artists and small businesses strengthens the very communities where you own or rent.

  
  

From all of us at STRUCTR, here’s to a season of warm lights, good neighbors, and homes that feel as special as the things you bring into them. 🌟