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  1. Events
  2. Massachusetts

Massachusetts Festivals, Craft Shows, Art Shows, Family & Kids Festivals 2026–2027.

Mass appeal: adventure, relaxation and rejuvenation, romance, arts and culture. Massachusetts offers an extraordinarily rich array of choices. So, think outside the....rock. (Plymouth, that is.) Of course, the Bay State honors tea, bays and parties! But, 382 other events beg the question: tried and true or new? You could start with the biggest: The Big E, Sowa Open Market - May and Lowell Folk Festival. And then strike out, independently, to sample all the rest that Massachusetts’ Festivals, Art Shows, Music Festivals and Craft Shows have to offer!

Featured Events
A Different Drummer Craft Fair September ~ Brewster

September 12 - 13, 2026

adifferentdrummercraft.com

(508) 364-5551
Drummer Boy Park, Route 6A - Brewster, MA

Juried, handmade craft-fine art show (no buy-resell, no manufactured & no reps). Great visibility on main road Route 6A in oceanside family park. Balanced by craft (5-7 vendors in the same category) for 50 spaces. 10x10 spaces, tents required, easy setup with drive up spaces, Friday afternoon early setup, overnight security. Heavily advertised in print, tourist publications, posters & flyers, & social media. Please see website for application & rules. Checks/money orders only. Contact Pat Daley for jury/sign up info today!

Fruitlands Fourteenth Craft Festival

September 19 - 20, 2026

thetrustees.org/place/fruitlands-museum

(978) 241-7463
Fruitlands Museum - Harvard, MA

Fruitlands Museum's picturesque grounds, overlooking the Nashoba Valley and the New Hampshire mountains, come alive with two 160' x 40' festival tents featuring 56 juried New England Artisans on September 19 & 20, 2026. The show's quality of handmade craft/art, museum offerings, and stunning views have made the festival a popular September destination. It is the perfect event for a fall outing to plan your holiday gifts for family and friends. Food is available from local food vendors, and Fruitlands Café.

Boxford Apple Festival

September 19, 2026

boxfordhistoricalsociety.org

(978) 764-4636
East Boxford Village - Boxford, MA

Large community event in East Boxford Village. Handmade crafts, food, music, historic house tours. Proceeds support maintenance of Holyoke-French House.

A Different Drummer Craft Fair October ~ Brewster

October 3 - 4, 2026

ADifferentDrummerCraft.com

(508) 364-5551
Drummer Boy Park, Route 6A - Brewster, MA

Juried, handmade craft-fine art show (no buy-resell, no manufactured and no reps). Great visibility on main road Route 6A in oceanside family park. Limited space per craft (5-7 vendors in one craft for balance). 10x10 spaces, tents required, easy setup with drive up spaces, Friday afternoon early setup, overnight security. Heavily advertised in print, radio, tourist publications, posters & flyers, & social media.

A Different Drummer Craft Fair at Lemon Tree Village

October 24 - 25, 2026

ADifferentDrummerCraft.com

(508) 364-5551
Lemon Tree Village Shops - Brewster, MA

20 craftspeople will be displaying their handcrafted items as a preview for the 4th Holiday Craft Fair at Monomoy High School in Harwich. Lemon Tree Village Shops are centrally located on the bay side of Cape Cod on historic Route 6A in Brewster, 1/2 mile from Drummer Boy Park towards Orleans. A Different Drummer has been invited to present a smaller, more personal craft fair on the premises. It is a sampler of the fullsize fairs. This busy location has constant flow of customers for the variety of shops. The craft fair will be arranged in the parking lot. See the application & guidelines on the website. Checks or money order payments only.

A Different Drummer Fourth Holiday Craft Fair

November 14, 2026

ADifferentDrummerCraft.com

(508) 364-5551
Monomoy Regional HS Gym - Harwich, MA

The 4th annual Holiday Craft Fair by A Different Drummer Craft Event! We bring the summertime craft fair indoors with full size 10x10 booths to display your full inventory for holiday shopping. Fair is juried and balanced by craft. 64 booths are available between gym and cafeteria but only 7 have electric. Well lit gym but battery powered lights are encouraged if you need lights. Bright cafeteria has 14 booths and is across from the gym. The same quantity/quality advertising is being done for the Holiday Craft Fair as for the summer fairs with print, radio and social media.

Rotary Club of Franklin Tri-County Craft Fair

November 14, 2026

Rotary Club of Franklin Facebook page

(508) 846-2590
Tri-County Regional Technical High School - Franklin, MA

Our 1st annual craft fair is Saturday, November 8th from 9am-3pm at Tri-County High School. Formerly run for 50 successful years by Franklin Newcomers and Friends. Admission is $4. Also collecting items for the Franklin Food Pantry!! Please support our community! Event features items for sale from artisans, a bake table, raffle table (everyone wins!) and 50/50 raffle. Proceeds are donated to local charities as voted on by members of the Rotary Club of Franklin.

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Fairs & Festivals in Massachusetts 2026–2027

Allston Village Street Fair Festival
September 27, 2026

Allston Village Street Fair Festival

6 City Blocks on Harvard Avenue from Brighton Ave, Allston/Boston, MA

Status: Updated 2/12/2026

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This Massachusetts Music Festival will have antique/collectibles, commercial/retail, corp./information, crafts, film, fine art, fine craft, flea market and homegrown products exhibitors, and 4 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sun 12pm-6pm. This event will also include: stage bands, street performances, facepainting, balloon artist, public street art.
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The Wayside Inn Apple Fest
October 3, 2026

The Wayside Inn Apple Fest

The Wayside Inn Historic Site, Sudbury, MA

Status: Updated 9/2/2026

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This Massachusetts Festival will have antique/collectibles, commercial/retail, crafts, fine art, fine craft and homegrown products exhibitors, and 10 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-2pm. This event will also include: meet bella the barn owl, obstacle course, bubble station, bobbing for doughnuts.
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SandwichFest
October 3, 2026

SandwichFest

Sandwich Village, Sandwich, MA

Status: Updated 6/12/2026

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This Massachusetts Festival will have crafts, fine art, fine craft and homegrown products exhibitors, and 10+ food booths. There will be Roving Performers with Local talent and the hours will be Sat 10am-3pm.
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The Big E
September 18 - October 4, 2026

The Big E

Eastern States Exposition, West Springfield, MA

Status: Updated 11/4/2025

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This Massachusetts State Fair will have commercial/retail, corp./information, crafts and fine craft exhibitors, and 100 food booths. There will be 3 stages with National, Regional and Local talent and the hours will be . Admission tickets are $8 - $25. This event will also include: circus, horse show, midway, daily & mardi gras parades.
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Wachusett Mountain OktoberFest
October 3 - 4, 2026

Wachusett Mountain OktoberFest

Wachusett Mountain, Princeton, MA

Status: Updated 8/30/2026

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This Massachusetts Ethnic Festival will have commercial/retail, fine art and fine craft exhibitors, and tba food booths. There will be 1 stage with Regional and Local talent and the hours will be . Admission tickets are $6 - $20.
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A Different Drummer Craft Fair October ~ Brewster
October 3 - 4, 2026

A Different Drummer Craft Fair October ~ Brewster

Drummer Boy Park, Route 6A, Brewster, MA

Web: ADifferentDrummerCraft.com

Status: Updated 12/1/2025

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This Massachusetts Craft Show will have crafts, fine art and fine craft exhibitors, and no food booths.
(508) 364-5551
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Smokey Chestnut Farm's Fall Craft Fair
October 2026 (dates not updated)

Smokey Chestnut Farm's Fall Craft Fair

Smokey Chestnut Farm Rescue, Norton, MA

Status: Updated 6/6/2025

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This Massachusetts Craft Show will have crafts, fine art and fine craft exhibitors, and no food booths. There will be 1 stage with Local talent and the hours will be Sat 11am-4pm. Admission tickets are $8 - $10. This event will also include farm decorated for halloween.
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Mashpee Oktoberfest Craft Fair
October 2026 (dates not updated)

Mashpee Oktoberfest Craft Fair

Mashpee Commons, Mashpee, MA

Status: Updated 9/25/2025

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This Massachusetts Festival will have antique/collectibles, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 20 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-4pm. This event will also include: kids' activities, bier garten.
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Littleton Oktoberfest
October 2026 (dates not updated)

Littleton Oktoberfest

36 King Street, Littleton, MA

Status: Updated 9/11/2025

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This Massachusetts Festival will have antique/collectibles, commercial/retail, crafts, fine craft, flea market and homegrown products exhibitors, and local food booths. There will be 1 stage with Regional talent and the hours will be Sat 11am-5pm.
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Mayo PTA Craft Fair
October 2026 (dates not updated)

Mayo PTA Craft Fair

Elementary School, Holden, MA

Status: Updated 9/15/2025

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This Massachusetts Craft Show will have crafts, fine art, fine craft and homegrown products exhibitors, and no food booths. Admission tickets are $2 - $3. This event will also include kids games and crafts.
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Horseshed Fair
October 2026 (dates not updated)

Horseshed Fair

First Church of Christ Unitarian, Lancaster, MA

Status: Updated 9/21/2025

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This Massachusetts Traditional Craft-Folk Event will have crafts, fine art and fine craft exhibitors, and no food booths. There will be 1 stage with Regional talent and the hours will be Sat 10am-4pm.
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Lakeville Arts and Music Festival
October 2026 (dates not updated)

Lakeville Arts and Music Festival

Junctions of Routes 105 & 18, Lakeville, MA

Status: Updated 8/8/2025

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This Massachusetts Music Festival will have crafts, fine art, fine craft and homegrown products exhibitors, and 2 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-4pm. This event will also include: pumpkin decorating, self chalk drawing opportunity.
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Foxboro Jaycees Fall Craft and Vendor Fair
October 2026 (dates not updated)

Foxboro Jaycees Fall Craft and Vendor Fair

Foxboro Common, Foxboro, MA

Status: Updated 8/7/2025

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This Massachusetts Festival will have antique/collectibles, commercial/retail, corp./information, crafts, film, flea market and homegrown products exhibitors, and 1 food booth. This event will also include bounce house and raffle table.
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Maynard Fest
October 2026 (dates not updated)

Maynard Fest

Memorial Park, Maynard, MA

Status: Updated 9/30/2025

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This Massachusetts Family & Kids Festival will have commercial/retail, corp./information, crafts and homegrown products exhibitors, and tba food booths. There will be 1 stage with Local talent and the hours will be Sat 9am-3:30pm. This event will also include children's activities.
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NRT's Harvest & Craft Fair
October 4, 2026

NRT's Harvest & Craft Fair

NRT's Sheep Pasture, North Easton, MA

Status: Updated 3/10/2026

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This Massachusetts Festival will have crafts, fine art and fine craft exhibitors, and 2 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sun 10am-2pm. Admission tickets are $5. This event will also include: family photo booth, animals, food trucks, non-profits, kids' games/activities.
5.00/5
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Haunted Biz Baz
October 2026 (dates not updated)

Haunted Biz Baz

Essex Street Pedestrian Mall, Salem, MA

Status: Updated 9/23/2025

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This Massachusetts Festival will have antique/collectibles, commercial/retail, corp./information, crafts, fine art, fine craft, flea market and homegrown products exhibitors, and 6 food booths.
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Worcester Armenian Festival
October 2026 (dates not updated)

Worcester Armenian Festival

Armenian Church of Our Saviour, Worcester, MA

Status: Updated 8/7/2025

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This Massachusetts Ethnic Festival will have no exhibit booths and no food booths. There will be 1 stage with International talent and the hours will be Sat 11am-5pm; Sun 11am-3pm. This event will also include: presentations, a church tour, musical and video productions, delicious food.
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Vintage Bazaar - Fall Edition
October 2026 (dates not updated)

Vintage Bazaar - Fall Edition

Crescent Farm, Haverhill, MA

Status: Updated 9/6/2025

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This Massachusetts Vintage will have antique/collectibles, crafts, fine art and fine craft exhibitors, and 12 food booths. There will be 1 stage with Regional talent and the hours will be Sat 10am-4pm; Sun 10am-3pm. Admission tickets are $10 - $20.
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Festival of the Hills
October 2026 (dates not updated)

Festival of the Hills

Town Park, Conway, MA

Status: Updated 9/25/2025

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This Massachusetts Festival will have crafts and fine craft exhibitors, and 10 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sun 10am-4pm.
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Fine Arts & Craft Show- October
October 10, 2026

Fine Arts & Craft Show- October

Sandwich Library Lawn, Sandwich, MA

Status: Updated 8/11/2026

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This Massachusetts Art Show will have crafts, fine art and fine craft exhibitors, and no food booths.
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23rd Annual Art Show & Sale
October 10 - 11, 2026

23rd Annual Art Show & Sale

Spencer Town Hall, Spencer, MA

Status: Updated 9/2/2026

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This Massachusetts Art Competition will have fine art exhibitors and no food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat-Sun 10am-4pm.
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Yarmouth Seaside Festival
October 10 - 11, 2026

Yarmouth Seaside Festival

Joshua Sears Field, South Yarmouth, MA

Status: Updated 8/17/2026

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This Massachusetts Festival will have crafts, fine art and fine craft exhibitors, and 12 food booths. There will be 1 stage with Local talent and the hours will be . This event will also include: live music, kids rides & games, fireworks, road race, beach bonfire, nature shows.
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Brookfield Apple Country Fair
October 2026 (dates not updated)

Brookfield Apple Country Fair

Town Common, Brookfield, MA

Status: Updated 8/8/2025

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This Massachusetts Craft Show will have crafts, fine art, fine craft and homegrown products exhibitors, and 6 food booths. There will be 1 stage with Regional and Local talent and the hours will be Sat 10am-4pm. This event will also include: apple pie baking contest, 50/50 raffle, lawn games.
3.57/5
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Fourteenth Worcester Food Truck & Craft Beer Festival
October 2026 (dates not updated)

Fourteenth Worcester Food Truck & Craft Beer Festival

Worcester Common, Worcester, MA

Status: Updated 3/25/2025

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This Massachusetts Food Festival will have crafts and flea market exhibitors, and 20 food booths. Admission tickets are $5 - $65. This event will also include: lawn games, music, shopping, and endless fun for everyone in the family.
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