MONADNOCK REGION, N.H. (MyKeeneNow) From craft fairs and concerts to light displays and Santa visits, holiday celebrations are underway across the Monadnock Region. Here is a date-by-date guide to help you plan your seasonal outings. Find full details and links for more information with each listing.

Saturday, Nov. 15, 2025

Holiday Bazaar — Hinsdale
9 a.m.–2 p.m., Hinsdale High School, Hinsdale
The Hinsdale High School Class of 2026 hosts its annual Holiday Bazaar, featuring local crafters, raffles, lunch and photos with Santa.
More info: hinsdale.k12.nh.us

Sewing Basics: Making Placemats — Jaffrey
11 a.m.–1 p.m., Jaffrey Public Library
Learn sewing basics with local seamstress Lindsey Bashelor and create holiday placemats. Registration required; space is limited.
More info: jaffreypubliclibrary.org

Wednesday, Nov. 19, 2025

Paint Your Own Holiday Cutting Board — Jaffrey
6–8 p.m., American Legion Post 11, Jaffrey
Create a custom holiday cutting board at this guided workshop.
Tickets: eventbrite.com (search event name)

Friday–Saturday, Nov. 21–22, 2025

Christmas Fair — Swanzey
Nov. 21, 4–6 p.m.; Nov. 22, 9 a.m.–1 p.m., First Congregational Church of Swanzey
The annual Christmas Fair offers wreaths, décor, baked goods, a Christmas café, crafts and a basket raffle.
More info: firstcongregationalchurchswanzey.com

Saturday, Nov. 22, 2025

Christmas on the Pond & Christmas Around the Bend — Marlow
9 a.m.–3 p.m., Marlow Village
More than 80 vendors fill Marlow Village and Perkins Academy with handmade goods, greenery, treats and live music. A shuttle runs between sites, and multiple luncheons are offered.
More info: Facebook pages “Christmas on the Pond” and “Christmas Around the Bend”

Peterborough Holiday Stroll — Peterborough
9 a.m.–2 p.m., Downtown Peterborough
Seven faith communities host concurrent fairs with crafts, baked goods and children’s activities.
More info: facebook.com/peterboroughholidaystroll

ConVal Craft Fair — Peterborough
9 a.m.–2 p.m., ConVal Regional High School
More than 90 vendors participate in this long-running craft fair.
More info: convalsd.net

Indoor Winter Market — Swanzey
9 a.m.–2 p.m., The Fieldhouse at Homestead Mills
Shop 50 vendors, enjoy kids’ activities, food, raffles and photos with Santa.
Vendor info: forms.gle (search event registration)

Photos with Monadnock Santa — Jaffrey
10 a.m.–1 p.m., Jaffrey Public Library
Free photos with Santa, with activities for kids while they wait.
More info: jaffreypubliclibrary.org

Sunday, Nov. 23, 2025

Holiday Workshops Kickoff — Keene
12–4 p.m., Stonewall Farm
Stonewall Farm begins its winter workshop series with wreath-making, Thanksgiving centerpieces, live demonstrations and a pop-up market.
More info: stonewallfarm.org

Winter/Christmas Doormat Workshop — Swanzey
1–3 p.m., Frogg Brewing
Create a festive doormat during this craft workshop.
More info: froggbrewing.com

Friday–Monday, Nov. 28–Dec. 1, 2025

Brattleboro Festival of Miniatures — Brattleboro, VT
12 p.m. daily, downtown Brattleboro
Window displays, dollhouses, model trains, puppet shows, pop-up markets and miniature art exhibits fill downtown.
More info: brattleboro.com/miniboro

Saturday, Nov. 29, 2025

Living Local Art Fair — Peterborough
10 a.m.–3 p.m., Unitarian Universalist Church
Thirty artists offer handmade gifts; proceeds support community suppers.
More info: uupeterborough.org

Makers Workshop: Angels, Beasts, Shepherds + More — Brattleboro, VT
1–4 p.m., River Gallery School of Art
A multigenerational craft workshop using diverse materials, with an option to contribute to a holiday window display.
More info: rivergalleryschool.org

Sunday, Nov. 30, 2025

A Charlie Brown Christmas with the Heather Pierson Trio — Jaffrey
The Park Theatre
The jazz trio performs the Vince Guaraldi score of the classic holiday special.
More info: theparktheatre.org

Monday, Dec. 1, 2025

A French Canadian Christmas Concert — Jaffrey
The Park Theatre
Josée Vachon and Patrick Ross present a traditional “réveillon”-style concert.
More info: theparktheatre.org

Friday, Dec. 5, 2025

Swanzey Festival of Lights Tour Kickoff — Swanzey
5:30–7 p.m., Swanzey Town Hall
Pick up the townwide tour map, enjoy lights, cocoa and candy canes, then visit decorated homes across Swanzey.
More info: townofswanzey.com

Monadnock Habitat “Nailed It!” Ugly Sweater Party — Swanzey
5–8 p.m., Frogg Brewing
A fundraiser featuring music, raffles and games to support Habitat’s local homebuilding initiative.
Tickets: tinyurl.com/26BY7PPZ
More info: monadnockhabitat.org

An Irish Christmas — Putney, VT
Next Stage Arts Project
John Doyle and Cathie Ryan perform Irish holiday music and stories.
More info: nextstagearts.org

Holiday Hoof Drive-Thru Light Display — Winchester
5–8 p.m., Draft Gratitude
A drive-through display featuring lights, festive scenes and retired draft horses. Also held Dec. 6–7.
More info: draftgratitude.com

Choir!Choir!Choir!: Un-Silent Night Sing-Along — Keene
7 p.m., The Colonial Theatre
An interactive holiday sing-along for all voices.
More info: thecolonial.org

Saturday, Dec. 6, 2025

A Very Swanzey Christmas — Swanzey
4–6:30 p.m., Whitcomb Hall
Letters to Santa, reindeer food, storytime, outdoor fire, treats and a 5 p.m. tree lighting followed by photos with Santa.
More info: townofswanzey.com

Holiday Hoof Drive-Thru Light Display — Winchester
5–8 p.m., Draft Gratitude
Second night of the drive-through light event.
More info: draftgratitude.com

Wednesday, Dec. 10, 2025

Holiday Trivia — Jaffrey
7 p.m., The Park Theatre
Seasonal trivia with eggnog and treats.
More info: theparktheatre.org

Friday, Dec. 12, 2025

A Yankee Christmas with Fred Marple & Rebecca Rule — Jaffrey
7 p.m., The Park Theatre
New England humorists share holiday stories and music.
More info: theparktheatre.org

Sunday, Dec. 14, 2025

Currier & Ives Cookie Tour — Monadnock Region
A regional tour of inns, shops and historic sites offering cookies, recipes and holiday decorations.
Maps available beginning Dec. 1 at The Park Theatre.
More info: theparktheatre.org

Annual Santa Party featuring “A Christmas Story” — Jaffrey
The Park Theatre
A long-running tradition featuring a free holiday movie and Santa visit.
More info: theparktheatre.org

“It’s a Wonderful Life” Screening — Jaffrey
The Park Theatre
The classic film returns for the holiday season.
More info: theparktheatre.org