Massachusetts: January & February - March - April - May - June - July/August - September - OCTOBER - November - December Check previous year if event is not yet updated to current year 2025 MASSACHUSETTS - OCTOBER 2025
Food & Wine Festivals, Shows & Local Events
(see also: 2024 - 2021 - 2020 - 2019 - 2018 - 2016)
October 2, 2025
The WhiskyX
Boston, Massachusetts
You’ll discover and taste some of the world’s most notable whiskies. Tastings, including some cocktails, are led by expert brand ambassadors and distillery representatives. October 16-19, 2025
15th Annual Martha's Vineyard Food & Wine Festival
Martha's Vineyard, Massachusetts
The flagship food, wine, and drink festival of Martha’s Vineyard, the Festival stays rooted in the Island’s rich tradition of farming and fishing, inviting you to meet local culinary talent, and the farmers, fishermen, oyster producers, and artisans they work with—adding guest chefs and vintners from around the world for a unique to the island celebration.
2024 MASSACHUSETTS - OCTOBER 2024
Food & Wine Festivals, Shows & Local Events
waiting for new datesOctober 5, 2024 - New Bedord Food Truck & Craft Beer Festival
New Bedford, Massachusetts
Food Truck Festivals of America. Featuring 20+ local (and delicious) food trucks. Also enjoy some of the best regional and national craft beers.
October 5, 2024 18th Annual NB Oktoberfest
New Bedford, Massachusetts
A fall tradition on the waterfront. Come and enjoy a variety of craft beers, interesting food trucks and live music. Attendees can expect a variety of craft and traditional brews as well as local food vendors throughout the evening. The ticket price covers admission to the event and allows us to book great musical acts to create the soundtrack to a great night. This event has attracted over 1,000 locals and travelers alike annually. Come in your finest lederhosen or jeans and a sweatshirt. The ambience is cool and the vibe is chill. All proceeds support at risk youth on the South Coast. October 5, 2024 SandwichFest Street Fair - Sandwich, Massachusetts
Hometown fun - Best Sandwich in Sandwich competition, Raffle, Pup Tricks Competition & Parade, Street Vendors & Farmers Market, Live Entertainment, Sandwich Bag Races, Sandwich Artisans Show & Sale, Heritage Museums & Gardens Antique Car Show and Sandwich Food Pantry donation location. October 10, 2024 - The Great Pumpkin Parade
New Bedford, Massachusetts
Rotch-Jones-Duff House & Garden Museum. Visit the grounds to see a display of Jack-O-Lanterns, carved with care by community members. Inside the mansion, children can participate in a scavenger hunt with prizes. Refreshments served. Suggested donation taken at site: $5 Individuals / $10 Family. This event is also part of AHA night. October 12, 2024 19th Annual New Bedford Seaport Chowder Festival
New Bedford, Massachusetts
Join us at the NB Chowder Fest where you can sample Clam Chowder, Seafood Chowder, Kale Soup and Stuffed Quahogs, from more than 25 area restaurants, all included in the price of your admission ticket. Live Music; YMCA Lobster Race; Local Beers, Wines; Soft Drinks and Desserts. October 12, 2024 Cape Cod Cranberry Day
East Sandwich, Massachusetts
Green Briar Nature Center and Jam Kitchen. Homemade cranberry dessert, chili & chowder for purchase. Cranberry cooking demonstrations in the 1903 Jam Kitchen. October 19-20, 2024 24th Annual Wellfleet Oysterfest
Wellfleet, Massachusetts
Wellfleet comes alive for a two-day celebration of the town”s famous oysters, clams and shellfishing traditions in this street party that brings together locals and visitors alike for a weekend full of food, frolic, and fun. October 26, 2024 39th Annual Essex ClamFest - Essex, Massachusetts
Several local restaurants will offer their favorite chowder recipes in a competition to determine who serves the best chowder on Cape Ann. Other activities will include arts & crafts, entertainment, food pavilion, Ipswich Ale station, non-profit tables, children's activities and a health fair.
2021 MASSACHUSETTS - OCTOBER 2021
Food & Wine Festivals, Shows & Local Events
waiting for new datesOctober 16, 2021 Annual Salem Harvest Fest - Salem, Massachusetts
Celebrate the season with a sampling of the finest wines, mead and beer.
2020 MASSACHUSETTS - OCTOBER 2020
Food & Wine Festivals, Shows & Local Events
waiting for new datesOctober 1-17, 2020 - Rockport Harvestfest - Rockport, Massachusetts
SPECIAL HARVESTFEST TO HOME EVENT FOR 2020 - SEE WEBSITE FOR DETAILS. From 10am to 5pm. New England food producers gather under a giant tent on one of Rockport’s historic working wharves to celebrate the best of local food with fresh seafood, pastries, cider doughnuts, chowder, small-batch jams, soups, and much more. A selection of local craft beers & wine, as well as soda from Rockport’s own Twin Lights Soda Company are on hand. Cooking demos, cookbook authors, the Rockport Farmers Market and plenty of live bluegrass, jazz, folk and celtic music are all part of the festival. October 8-11, 2020 The Taste of WGBH Food & Wine Festival
Boston, Massachusetts
Building on the success of the past, we’re once again collaborating with some of the finest farms, producers, restaurants, wineries, and breweries in this region. Among the new additions to our program this year is an extra day of indulgence on Sunday with our first-ever Brunch Bar. Join us for a weekend full of festivities that will not only satisfy your palate but also enrich your understanding of New England’s food culture. October 18, 2020 James Beard Foundation's Taste America
Boston, Massachusetts - A VIRTUAL DINING EVENT FOR 2020.
James Beard Foundation’s Taste America national epicurean tour, featuring one-night-only collaborative dinners. Enjoy a unique, one-night only menu created by a Taste America All-Star joined by an elite team of notable local chefs. These exclusive dining events are perfect for the food enthusiast, as well as offering ideal entertaining opportunities for executives, clients, media, and VIPs. See website for ticket prices and details for each city.
2019 MASSACHUSETTS - OCTOBER 2019
Food & Wine Festivals, Shows & Local Events
waiting for new datesOctober 6, 2019 - Pudding Hollow Pudding Festival (and Pie Extravaganza! - Hawley, Massachusetts
EVENT HELD EVERY 5 YEARS. Around 1780, according to legend, the hamlet of Hawley, Massachusetts, held a pudding contest to determine who could make the largest pudding in town. The eventual winner, Abigail Baker, created a hasty pudding in a five-pail kettle (basically enough pudding to serve about 300 people, the approximate population of Hawley then and now). She was thereafter known as Pudding Head, and the area of town in which she lived is still called Pudding Hollow. In 2004, the contest was revived, although today flavor rather than size is the key criterion in selecting a winner. Every five years, the town’s historical society, the Sons & Daughters of Hawley, holds a pudding festival that includes the contest, a homemade lunch, a pudding parade, a festive entertainment, and of course the crowning of the new Pudding Head. This year’s festival will take place on Sunday, October 6. Puddings (along with transcribed recipes) are due at 11 a.m. that day. The festival is free, although donations are requested for entering the contest and for the lunch. Food-related prizes are donated by a variety of businesses. All funds raised go toward the ongoing restoration of the Hawley Meeting House as a community center. This event is full of New England fun; the Sons & Daughters call it “a little bit country and a little bit Julia Child.” October 12, 2019 - Local Craft Spirits Festival
Cambridge, Massachusetts
Sustainable Business Network’s Local Craft Spirits Festival. The Festival will gather hundreds of local spirits fans to celebrate together with dozens of local vendors and hundreds of products! Participate in cocktail demos, enjoy local food, and help choose Boston’s best local craft Mixologist at our Local Craft Cocktail Throwdown. Hosted by SBN and the Boston Local Food Committee, Local Craft Spirits Festival premiered as New England’s first ever spirits festival of exclusively local spirits and artisan brews. Get ready to indulge in more than 100 unique samples of local food and beverage, so come taste, discover, socialize, and network with dozens of local distilleries, cideries, meaderies, breweries, artisan beverage brewers, and local food producers, all while savoring local music and celebrating local spirits! SBN's Local Craft Spirits Festival is affiliated with, and a major fundraiser for, the Annual Boston Local Food Festival. October 19, 2019 Ski Butternut Food Truck & Craft Beer Festival
Great Barrington, Massachusetts
Food Truck Festivals of America. Featuring 20+ local (and delicious) food trucks. Also enjoy some of the best regional and national craft beers. October 22, 2019 - Taste of the Region - Franklin, Massachusetts
Sample a variety of delicacies offered from around the region. This fun-filled food festival features an eclectic mix of up to twenty restaurants serving dishes sure to tease your taste buds. Enjoy wonderful music and bid on exciting items in our silent auction. This is an event you won't want to miss! Tickets cost $10 in advance or $15 at the door.
2018 MASSACHUSETTS - OCTOBER 2018
Food & Wine Festivals, Shows & Local Events
waiting for new datesOctober 6-7, 2018 - 15th Annual Cranberry Harvest Celebration
Wareham, Massachusetts
Hosted by the A.D. Makepeace Company and co-sponsored by the Cape Cod Cranberry Growers’ Association and Ocean Spray Cranberries, Inc. Visitors are treated to demonstrations of the wet cranberry harvest, cooking demonstrations, an enormous tent full of juried crafters, paddleboat rides on scenic Tihonet Pond, food vendors, music, and more. A great way to see and learn about the picturesque cranberry harvest, while enjoying some old-fashioned family fun. Admission is $10, $5 for seniors and military, and children under 7 are admitted free. Free Parking. No pets, no dogs please. October 8-14, 2018 Cape Cod Restaurant Week 2018
Cape Cod, Massachusetts
During Cape Cod Restaurant Week, the best restaurants from Falmouth to Wellfleet are offering three- and four-course exhibition menus for $25, $30 or $35. Revisit an old favorite or find a new one!
2016 MASSACHUSETTS - OCTOBER 2016
Food & Wine Festivals, Shows & Local Events
waiting for new datesOctober 13, 2016 Fresh Taste - Wellesley, Massachusetts
The Natick Visiting Nurse Association (Natick VNA), the area’s premier free-standing, not-for-profit home health care agency. Annual Fresh Taste benefit from 6pm until 9pm at Elm Bank Reservation, Wellesley. All proceeds generated at Fresh Taste will benefit Natick Visiting Nurse Association. October 15, 2016 North Shore Food Truck Festival
Stoneham, Massachusetts
The 2nd Annual North Shore Food Truck & Craft Beer Festival! New England's most popular food trucks will be present along with multiple breweries. | 
