Most of Jamaica Plain's handmade holiday shopping happens in two rooms over nine days this year. The First Church in Jamaica Plain Holiday Craft Fair opens on Saturday, December 5, with more than 30 local makers. One week later, on December 12 and 13, Spontaneous Celebrations hosts its JP Holiday Market with more than 40 artists and small businesses. That adds up to more than 70 artists, makers and small businesses across three selling days. On most of the other days, holiday shopping in JP happens at the regular storefronts, and two of them were singled out this year.

The rest of November is quieter and runs on small weekly events. Here is what's on before the first market weekend.

The run-up is small and close to home

Tonight, Thursday, November 19, JP Chess meets at J.P. Licks, 659 Centre St., from 6 to 9 p.m. It's a weekly listing on the JP Centre/South Main Streets calendar, and it's on again next Thursday, November 26.

Tomorrow, Friday, November 20, the same calendar lists a Thanksgiving Dinner on a Budget Workshop from 5:30 to 6:30 p.m. at 120 South St. The timing makes sense, six days before the holiday, which falls on November 26.

The weekend's main events are at the Arnold Arboretum. The Arboretum's event calendar lists these:

• Saturday, November 21: a family wellness walk from the Hunnewell Building, plus an owl walk that starts at the Flora Way Gate.
• Sunday, November 22: a lecture in Hunnewell Lecture Hall on the regal lily and the plant collector E.H. Wilson.

The calendar doesn't list times for these, so check the event pages before you head over. The Arboretum comes up again on December 5.

December 5 stacks up at Eliot Street and the Arboretum

The First Church in Jamaica Plain is at 6 Eliot Street. Its Holiday Craft Fair runs Saturday, December 5, from 11 a.m. to 5 p.m. The church says to expect more than 30 local artists and makers selling handmade crafts and art, along with live music and a children's bake sale.

The Arboretum's calendar also has two events that Saturday: another family wellness walk at the Hunnewell Building and a lecture on hemlocks in Hunnewell Lecture Hall. The JP Centre/South Main Streets calendar shows two more events that day. Of all the Saturdays between now and mid-December, December 5 has the most going on.

The fair is a one-day event with six hours of selling. Anything you want from those 30-plus makers has to be bought between 11 and 5 that Saturday.

December 12 and 13 at 45 Danforth Street

The second weekend is bigger and spread over two days. The JP Holiday Market at 45 Danforth St. runs from noon to 5 p.m. on Saturday, December 12, and Sunday, December 13. The event listing names Spontaneous Celebrations as host, and the organization's vendor page confirms it's selling space for its 2026 JP Holiday Markets.

The listing gave October 31 as the vendor application deadline. The listing includes jewelry, art, handmade knits, holiday cards, candles, crystals, body care, books, kilim rugs, pottery, pet treats, vintage goods, handmade soaps, prints and fiber arts.

Here's how the two weekends compare:

Because the Danforth Street market has a Sunday, it's the easier one to work around. If December 5 is already full, the following weekend gives you two afternoons to make up for it.

The shops that carry the weeks in between

The markets cover three days. The other weeks of December depend on JP's year-round storefronts, and two of them got public recognition this year.

On South Street, Sweet Pea & Sage, the florist at 166 South St., was named JP Centre/South Main Streets' 2026 Business of the Year, as Jamaica Plain News reported on November 3. In the Main Streets announcement embedded in that article, the group praised the shop's arrangements and merchandise and said it brings "just as much life and vitality to South St in #JamaicaPlain." The shop is a short walk from the Thanksgiving workshop at 120 South St.

City Feed and Supply is on the City of Boston's list of 2026 Legacy Business Award winners from Jamaica Plain. The city announced those winners on June 4. To qualify, a business has to have been located in Boston for at least ten years and contribute to its community's cultural, historical and societal fabric. Nominations for the fifth annual round ran from September 23 through October 30, 2026, as Caught in Eastie reported. The next class of honorees comes from that pool. You can see the full list of past winners on the city's Legacy Business Program page.

The ten-year rule fits other JP businesses too. Fat Ram's Pumpkin Tattoo marked its 25th anniversary this fall, and Jamaica Plain News reported that a celebration was planned at the Midway Cafe on October 25.

Some storefronts are new. In September, Jamaica Plain News reported that Edwin Barber Studio had opened at 636 Centre St., in a building that had been empty for a long time. That's the first holiday season for that address in some time.

Two other details will help with your planning. The South Street florist and the Centre Street shops are part of the JP Centre/South Main Streets district, and the Main Streets calendar is where the district's events get posted. Further along, the group once called Hyde/Jackson Square Main Street now goes by Three Squares Main Street JP, so look for that name.

The Washington Street storefront that's still a year away

The holiday calendar also gives you a look ahead to next year. Happy Market has applied for an alcohol license to move into the retail space at the new Doyle's development, 3474 Washington St., according to Jamaica Plain News on October 20. As part of the public process, the market was scheduled to appear before the Jamaica Plain Business and Professional Association on October 21.

Lee Goodman of WaterMark Development told the outlet the move depends on getting the license. Between permitting and building out a space of more than 5,000 square feet, he said the best case is an opening about a year from the date of the report. That puts the earliest opening around fall 2027, so this December's shopping will still be at Eliot Street, Danforth Street and the existing storefronts.

If you're thinking about how Jamaica Plain's commercial corridors are changing, or you just want to compare notes on Washington Street, Sean Preston is happy to talk it through. Let's Connect.