Community business calendar
Meet other owners, learn something new and find your next customer.
58 upcoming events · Confirm details with the organizer before attending.
- Oct62026Business Workshop / Networking
2026 Workshop: LinkedIn, Your Digital Front Door
Business education workshop focused on LinkedIn as a professional and business-facing digital presence.
ChicopeeHosted by Chicopee Chamber of Commerce · See registration page · In PersonEvent details - Oct62026Business / Coworking / NetworkingFree
Chicopee Chamber Coworking Day - October 6
Free coworking day open to entrepreneurs and others seeking a community workspace and informal networking.
10:00 AM – 4:00 PMChicopeeHosted by Chicopee Chamber / City of Chicopee Office of Economic Development · Free · In PersonEvent details - Oct72026Farmers Market / CommunityFreeVendor spots
Center Fresh Farmers Market
Community farmers market.
See city calendarChicopeeHosted by City of Chicopee · Free admission · In PersonEvent details - Oct82026Business / Networking / Community
Multi Chamber Power Hour
Multi-chamber networking featuring regional nonprofits.
8:00 AM – 9:30 AMHolyokeHosted by Greater Holyoke & Chicopee Chambers · Registration · In PersonEvent details - Oct82026Business / Networking
Westfield Bank After 5
Regional after-work networking mixer.
5:00 PM – 7:00 PMHolyokeHosted by Greater Holyoke Chamber / Westfield Bank · Registration · In PersonEvent details - Oct102026Community / Grand OpeningFree
Cancer Connection THRIFT SHOP Grand Opening
Community grand opening and nonprofit thrift-shop event
11:00 AM – 2:00 PMSpringfieldHosted by Cancer Connection · Free / see organizer · In PersonEvent details - Oct112026Sports / Youth / Community
Girls VolleyHall Classic Elite
Elite high-school volleyball tournament featuring teams from across the Northeast.
SpringfieldHosted by International Volleyball Hall of Fame · See event page · In PersonEvent details - Oct122026Family / Fall FestivalFree
Holyoke Mall Fall-A-Palooza
Free fall family event with face painting and entertainment.
10:30 AM – 12:30 PMHosted by Holyoke Mall · Free · In PersonEvent details - Oct152026Business / Coworking / NetworkingFree
Chicopee Chamber Coworking Day - October 15
Free coworking day open to entrepreneurs and individuals, hosted with Chicopee economic development.
10:00 AM – 4:00 PMChicopeeHosted by Chicopee Chamber / City of Chicopee Office of Economic Development · Free · In PersonEvent details - Oct162026Community / Business / Networking
Made in Chicopee Tour
Community/chamber tour highlighting Chicopee businesses and manufacturing.
ChicopeeHosted by Chicopee Chamber of Commerce · Registration · In PersonEvent details - Oct172026Community / History / AutoVendor spots
From Muskets to Motors: 250 Years of Innovation Antique Car and Motorcycle Show
Antique car and motorcycle show with food and information vendors
11:00 AM – 2:00 PMHosted by Friends of Springfield Armory National Historic Site · See event page · In PersonEvent details - Oct192026Business / Community Resource
2026 Monthly Small Business Advising Sessions - October
Small-business advising and entrepreneur support
10:00 AM – 4:30 PMHosted by Small Business Advising Partners · See event page · In PersonEvent details - Oct212026Farmers Market / CommunityFreeVendor spots
Center Fresh Farmers Market
Community farmers market.
See city calendarChicopeeHosted by City of Chicopee · Free admission · In PersonEvent details - Oct222026Arts & Culture / Fundraiser
Spellbound: Fall Fundraiser 2026
Victorian-inspired fall fundraiser at the museums.
6:00 PM – 8:30 PMHosted by Springfield Museums · $100 · In PersonEvent details - Oct222026Family / Halloween
City of Chicopee Spooktacular
City Halloween community celebration.
4:00 PM – 7:00 PMChicopeeHosted by City of Chicopee · See city information · In PersonEvent details - Oct222026Business / Community / Networking
Homewood Suites Ribbon Cutting and After 5
Ribbon cutting and tours at 11 AM followed by an After 5 networking gathering from 5-7 PM.
11:00 AM / 5:00 PM – 7:00 PMHolyokeHosted by Greater Holyoke Chamber · See registration page · In PersonEvent details - Oct242026Community / Nonprofit
Reese Fund Day of Compassion
Community giving event supporting emergency medical care for animals
10:00 AM – 2:00 PMSpringfield AreaHosted by Foundation for TJO Animals · See event page · In PersonEvent details - Oct242026Family / Arts & CultureFree
Halloween at the Museums
Costumes, gallery trick-or-treating, face painting, bubbles, crafts and family activities.
10:00 AM – 5:00 PMHosted by Springfield Museums · Free with museum admission · In PersonEvent details - Oct242026Business / Women Entrepreneurs / NetworkingVendor spots
Free to Flourish - Women Entrepreneur Conference
Women entrepreneur conference focused on personal and business growth, local entrepreneur speakers, networking, lunch, and an exhibitor/vendor showcase.
10:00 AM – 4:00 PMSpringfieldHosted by Tatiana Cole · See Eventbrite · In PersonEvent details - Oct282026Business / Networking
2026 Business After Hours with Westfield Bank
Chicopee Chamber Business After Hours networking event with Westfield Bank.
ChicopeeHosted by Chicopee Chamber of Commerce / Westfield Bank · See registration page · In PersonEvent details - Oct302026Science / Education
Space for Everyone: Astronomy Symposium
Astronomy symposium and educational program.
12:00 PM – 8:00 PMSpringfield / VirtualHosted by Springfield Museums · $50 · VirtualEvent details - Nov12026Community / Vendor Expo / Creative BusinessVendor spots
Quince Fest 2026
Quince and Sweet 16 expo featuring local event-industry vendors including photographers, DJs, MCs, makeup artists, gowns, cakes, caterers, planners, decorators and photo booths.
2:00 PM – 6:00 PMSpringfieldHosted by Mary “Ivy” Irizarry / Ivy’s Events · $5 listed; Eventbrite currently shows sales ended · In PersonEvent details - Nov42026Farmers Market / CommunityFreeVendor spots
Center Fresh Farmers Market
Community farmers market.
See city calendarChicopeeHosted by City of Chicopee · Free admission · In PersonEvent details - Nov62026Community / Networking
Coffee and Conversation at WWLP
Community and business networking event.
Chicopee / Springfield AreaHosted by Chicopee Chamber of Commerce · See registration page · In PersonEvent details - Nov62026Career / Business / NetworkingVendor spots
Massachusetts Sports & Entertainment Career Expo
Career expo connecting attendees with hiring managers and executives from sports and entertainment organizations; includes networking and a Springfield Thunderbirds game ticket.
4:00 PM – 6:00 PMSpringfieldHosted by TeamWork Online / Springfield Thunderbirds · $38-$42 plus Eventbrite fees · In PersonEvent details - Nov72026Community / Fundraiser / Gala
City of Bright Nights Ball
Annual black-tie fundraiser supporting Spirit of Springfield community programming
6:30 PM – 12:00 AMHosted by Spirit of Springfield · Ticketed · In PersonEvent details - Nov82026Community / Music
U.S. Army Field Band Concert
Community concert presented through Spirit of Springfield
2:00 PMHosted by Spirit of Springfield · See organizer · In PersonEvent details - Nov82026Community / Wedding Expo / Vendor MarketplaceVendor spots
Western New England Fall Bridal Show 2026
Regional bridal show bringing wedding consumers together with event, hospitality and creative-industry vendors.
11:00 AMSpringfieldHosted by See event page · See Eventbrite/event page · In PersonEvent details - Nov142026Community / Holiday MarketFreeVendor spots
19th Annual Holiday Pawzaar
Free family-friendly holiday market and fundraiser
10:00 AM – 3:00 PMSpringfield AreaHosted by Foundation for TJO Animals · Free · In PersonEvent details - Nov162026Business / Community Resource
2026 Monthly Small Business Advising Sessions - November
Small-business advising and entrepreneur support
10:00 AM – 4:00 PMHosted by Small Business Advising Partners · See event page · In PersonEvent details - Nov182026Farmers Market / CommunityFreeVendor spots
Center Fresh Farmers Market
Community farmers market.
See city calendarChicopeeHosted by City of Chicopee · Free admission · In PersonEvent details - Nov192026Business / Community ResourceFree
BizGrow Small Business Legal & Technical Assistance Conference
Free appointments with business attorneys and technical-assistance providers
12:00 PM – 3:00 PMSpringfield AreaHosted by Lawyers for Civil Rights / BizGrow · Free · In PersonEvent details - Nov212026Family / Holiday / Arts
Grinchmas at the Springfield Museums
Holiday décor, festive science/art activities and Grinch-themed experiences.
11:00 AM – 5:00 PMHosted by Springfield Museums · Museum admission / see event page · In PersonEvent details - Nov232026Community / Fundraiser
17th Annual March for the Food Bank
Annual community event supporting the Food Bank of Western Massachusetts
7:00 AM – 4:00 PMSpringfieldHosted by Food Bank of Western Massachusetts · See event page · In PersonEvent details - Nov252026Community / Holiday
Bright Nights at Forest Park
Annual holiday lighting experience; closed Nov. 30 and Dec. 1
5:00 PM – 9:00/10:00 PMSpringfieldHosted by Spirit of Springfield · $30/car standard; advance purchase required · In PersonEvent details - Nov302026Community / Fitness / Holiday
Bright Nights 5K Road Race
Annual road race through the Bright Nights holiday displays
6:30 PMSpringfieldHosted by Spirit of Springfield · See registration page · In PersonEvent details - Dec32026Entrepreneurship / CommunityFree
Innovate413 Shark School — Fall 2026
Free program for entrepreneurs actively building businesses
5:00 PM – 7:00 PMSpringfieldHosted by Innovate413 · Free / registration · In PersonEvent details - Dec52026Community / Holiday / ParadeVendor spots
Springfield Holiday Lights Parade
Holiday parade; businesses and nonprofits may apply to participate after Nov. 1
5:30 PMHosted by Springfield Jaycees · Spectator event; participant fees apply · In PersonEvent details - Dec52026Sports / Community / Holiday
Springfield Thunderbirds - Teddy Bear Toss
Thunderbirds hockey game featuring the annual Teddy Bear Toss promotion.
6:05 PMSpringfieldHosted by Springfield Thunderbirds / MassMutual Center · Ticketed · In PersonEvent details - Dec62026Sports / Community
Basketball Hall of Fame Classic 2026
Basketball Hall of Fame Classic at the MassMutual Center.
1:00 PMSpringfieldHosted by Naismith Basketball Hall of Fame · Ticketed · In PersonEvent details - Dec132026Community / Holiday / MusicFree
215th Army Band Holiday Concert
Free annual holiday concert for families and the community
2:00 PMHosted by Spirit of Springfield · Free with ticket · In PersonEvent details - Dec292026Sports / Family
Harlem Globetrotters: Rivalry Tour
Family basketball entertainment event.
7:00 PMSpringfieldHosted by Harlem Globetrotters / MassMutual Center · Ticketed · In PersonEvent details - Jan82027Business / Community / Nonprofit
2027 January Rise & Shine Breakfast: Celebrating Nonprofits
Regional breakfast focused on nonprofit organizations and community connections
8:00 AM – 9:30 AMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - Jan142027Business Workshop
Turn Customers into Champions - Chamber + SCORE Workshop
Small-business workshop on customer advocacy and growth
1:30 PM – 3:00 PMSpringfieldHosted by Springfield Regional Chamber + SCORE · Registration required · In PersonEvent details - Jan252027Business / Civic / Networking
2027 Government Reception
Business and civic networking reception
4:30 PM – 6:30 PMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - Feb112027Business Workshop
AI Tools, Real Business Results - Chamber + SCORE Workshop
Practical AI tools workshop for small businesses
1:30 PM – 3:00 PMSpringfieldHosted by Springfield Regional Chamber + SCORE · Registration required · In PersonEvent details - Mar52027Business / Regional
2027 OUTLOOK
Regional business and economic outlook event
11:00 AM – 2:00 PMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - Apr12027Business Workshop
Build Your Brand, Boost Your Sales - Chamber + SCORE Workshop
Branding and sales workshop for small businesses
1:30 PM – 3:00 PMSpringfieldHosted by Springfield Regional Chamber + SCORE · Registration required · In PersonEvent details - Apr82027Business / Community
2027 April Rise & Shine Breakfast: Chasing the American Dream
Regional business/community breakfast
8:00 AM – 9:30 AMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - May72027Business / Civic / Community
2027 Mayors Forum
Regional civic and business forum
8:00 AM – 9:30 AMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - May202027Business / Networking / Community
2027 Fire & Ice
Regional networking event
4:00 PM – 6:30 PMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - Jun92027Business / Community
2027 Springfield Regional Chamber Spotlight and Annual Meeting
Annual regional business-community gathering
4:00 PM – 6:30 PMSpringfield AreaHosted by Springfield Regional Chamber · Registration required · In PersonEvent details - Invalid DateNaNNaNArts & Culture / Workshop
Urban Sketching: Principles & Techniques
Hands-on urban sketching workshop.
10:00 AM – 12:00 PMHosted by Make-It Springfield · See organizer · In PersonEvent details - Invalid DateNaNNaNArts & Culture / Workshop
Collage Workshop / Collage Club
Recurring community collage-making workshop.
4:00 PM – 6:00 PMHosted by Make-It Springfield · See organizer · In PersonEvent details - Invalid DateNaNNaNHoliday / Community / FundraiserVendor spots
Festival of Trees
Annual holiday tree display and community fundraiser.
Varies – VariesSpringfieldHosted by Springfield Boys & Girls Club / MassMutual Center · See event page · In PersonEvent details - Invalid DateNaNNaNCommunity / Workshop
RAD Springfield Bike Workshop
Drop-in bike workshop for questions, repairs and community learning.
2:00 PM – 6:00 PMHosted by Make-It Springfield · See organizer · In PersonEvent details - Invalid DateNaNNaNArts & Culture / CommunityFree
Free Open Studio at Make-It Springfield
Free open-studio hours for community making and creative work.
Varies – VariesHosted by Make-It Springfield · Free · In PersonEvent details - Invalid DateNaNNaNMusic / Community
Jason Schwartz Jazz Series
Recurring downtown jazz series with changing featured musicians.
8:00 PM – 10:00 PMSpringfieldHosted by Theodore's / Downtown Springfield · See venue · In PersonEvent details