Upcoming Events In Western Mass

We strive to post the most current and accurate event information but changes and cancellations do occur so please check the official event website to confirm all details.

When you think back to some of your favorite childhood moments, very few of them probably happened when you were sitting at home watching TV. Instead, your most poignant memories probably revolve around that time you ended up with the home run ball at a baseball game, and the crowd cheered and you felt like a rock star, or at least like Babe Ruth.

Or maybe it was that time your family attended The Big E together and your dad bought you cotton candy and let you get all sticky-faced, and you watched your mom beat the midway games, and you felt like your heart was going to overflow with contentment and happiness.

In Western Massachusetts, events bring us together to celebrate our successes and recollect on our heritage. We’ve put together a list of some of the top yearly events in Massachusetts, things we and our local friends love doing to feel connected to our area and our community.

Top Yearly Western Massachusetts Events

Because of the beautiful area where we live, there are distinct Western Massachusetts-specific events that take place in each and every season. From leaf peeping in the fall to river rafting in the spring to skiing in the winter, you can find a wide range of things to do throughout the year, and some of our local events reflect the joyous beauty of our seasons.

Top Western Massachusetts Events for Spring

Springfield Annual Pancake Breakfast

Does anything scream “neighborly get-together more than a pancake breakfast? If your mouth is already watering over the thought of fluffy, buttery, syrupy goodness, you’re not going to want to miss the Springfield Annual Pancake Breakfast, typically hosted in May in downtown Springfield.

Bring your appetite, because it’s billed as the World’s Largest Pancake Breakfast, and be ready to feast on both good food and friendly conversation.

Paradise City Arts Festival (Northampton)

This Paradise City Arts Festival is ranked among the best in the country, and includes exhibits from more than 250 artists in all mediums. Artists flock to Western Massachusetts from around the country to be part of this visually dazzling display.

Come out to enjoy the weather that’s not quite summer, not quite spring, and stay to buy way too much from the vast selection of contemporary art pieces on display.

Brimfield Outdoor Antique Show

With spring in the air, you’ll want to get out and enjoy the largest outdoor antique and collectible show in the country. The Brimfield Outdoor Antique Show features over 5000 dealers throughout the quaint country town of Brimfield. And once is never enough – they do this in July and September, too!

Top Western Massachusetts Events for Summer

Baseball Season Opening Night

Baseball is the quintessential American pastime, and there’s really nothing that can top the nostalgia of being present on opening night.

The Westfield Starfires and Valley Blue Sox will kick off their seasons right at the start of the summer, and both promise to bring plenty of excitement to the community. Be sure you arrive ahead of gametime to root, root, root for the home team.

Yankee Candle Christmas in July

We love the unforgettable scents of the holiday season. Fir and balsam, spicy gingerbread, warm apple cider – the list could go on and on.

So naturally, Christmas in July is a must. At the flagship Yankee Candle Village, you can enjoy the holiday season, snap selfies with Santa (who might have traded in his traditional red velvet for a more relaxed Hawaiian shirt vibe) and enjoy crafting with Mrs. Claus.

It’s just what you need to get a little dose of holiday spirit and deal with the fact that you probably won’t be decorating your tree for at least a couple more months.

Basketball Hall of Fame Enshrinement

Meet Basketball’s best in the birthplace of the sport! Each summer, the Naismith Memorial Basketball Hall of Fame enshrines the best in the sport in Springfield. Rub elbows with the greatest to play the game and save time for a tour of the Hoop Hall.

Top Western Massachusetts Events for Fall

The Big E

Would this even be a reliable listing of Western Massachusetts events if The Big E weren’t included? The community gathering, more formally known as the Eastern States Exposition, is the biggest and best county fair you could imagine.

Every fall, The Big E brings together amazing food, parades, musical entertainment, agricultural exhibitions, car shows and more. There’s so much to see, do and taste – you’ll need more than one day to fully enjoy all The Big E has to offer.

Six Flags New England’s Fright Fest

Each autumn, Six Flags New England transforms into a fright-filled funzone for teens and adults. You’ll find scary shows, walk-through attractions and thrill rides that make the most of the season.

Top Western Massachusetts Events for Winter

Springfield Thunderbirds

The Springfield Thunderbirds are a professional ice hockey team in the American Hockey League affiliated with the National Hockey League’s St. Louis Blues. Based in Springfield, Massachusetts, the Thunderbirds play their home games at the MassMutual Center.


Springfield, Parade of the Big Balloons

Can’t quite make it to New York City for the Thanksgiving parade? We’ve got you covered, with the Parade of the Big Balloons in downtown Springfield.

Enjoy bands, community gatherings and balloons that represent the best Western Mass has to offer – our favorite is definitely the 75-foot Cat in the Hat balloon.

Bright Nights at Forest Park

Holiday memories are made at Bright Nights at Forest Park. It’s just not the holiday season until you’ve driven through this holiday lighting extravaganza! Look for Santa’s Magical Forest, Dinosaur World and Seuss Land – it’ll become an annual tradition after the first mile.

Holyoke St. Patrick’s Day Parade

Run, walk or float over to the Holyoke St. Patrick’s Day Parade. This celebration of Irish heritage brings more than 400,000 guests to the community for a parade, music, food and fun.

It also includes traditional performances by the Holyoke Caledonian Pipe Band and the Road Race, Western New England’s largest race (featuring a 10k, a 2 mile walk and a Kids Fun Run).

Community events help us to celebrate what we have in common – a love of the arts, of sport, of nature. The human connection these events create is so important to both mental and physical well-being.

If you’d like to learn more about these community events and dozens of others coming up in Western Mass, or about the top yearly events in Massachusetts, check out our Events listings and customize a schedule just for you. Or, contact us, and let our team of knowledgeable locals help you prepare for a fun and unforgettable Western Mass adventure.

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Springfield Jazz & Roots Festival

August 14 @ 1:00 pm - 10:00 pm EDT

2021 marks the 8th season of Springfield Jazz & Roots Festival produced by Blues to Green, an annual celebration that brings thousands of people together in the heart of Springfield, MA. This internationally heralded festival has become a powerful expression of civic pride, uniting our region’s diverse cultural communities through music, art, education, and revelry.

This year’s festival will begin at the Wood Museum of Springfield History, where ticket holders will have free access to the ‘Horn Man: The Life and Musical Legacy of Charles Neville’ exhibit. At the museum, festival attendees will be invited to participate in a free percussion workshop that will culminate in a parade led by Henri Smith ending at the stage of our kick-off performance beginning at 1:00 PM.

10:00 am: Museum opens. Enjoy FREE access to “Horn Man: The Life and Musical Legacy of Charles Neville.” at the Wood History Museum.

10:30 am: Family-friendly art activities begin on the lawn and patio of the Wood History Museum.

11:30 am: Join Berkshire Bateria for an all-ages percussion workshop and prelude to the parade. Don’t worry; we’ve got all of your drum needs covered!

12:30 pm: The Second Line Parade leaves the museum and is led by grand marshall Henri Smith & New Orleans Friends and Flavours. We are making our own hybrid of a parade that we are calling Samba meets Second Line thanks to the participation of Berkshire Bateria. Everyone is welcome to march in the parade down to the stage of our kick-off festival performance!

A brief history…

Second lining has been called “the quintessential New Orleans art form.” Historically, the African-American community began second lines as neighborhood celebrations and honoring the deceased. The neighborhood organizations offered social aid to freed slaves, such as loans and insurance, and used the second lines to advertise.

There are two parts to the second line. The first line is made up of a grand marshall or parade leader, the band, and whoever is being honored. The strutting revelers who fall in behind are referred to as the second line. The leads of the parade carry decorated umbrellas while the other participants shake handkerchiefs and dance. A brass band plays and is the heartbeat that gets everyone dancing.

In addition to the awesome music, parade, and art activities, we are producing a three-part Speaker Series with the generous support of New England Public Media and Valley Venture Mentors.  Of course, these engaging talks with guest speakers are free and will be sprinkled throughout the day.

We have added a second stage and a few new acts to the lineup, including a high-energy break dancing battle. In addition to that, we will host a pop-up vaccine clinic in partnership with the City of Springfield to provide FREE vaccines at the festival to anyone who wants one. In addition to the vaccine, any Springfield residents who participate in this program will receive a $25 gift card to either Walgreens, Big Y, or Stop & Shop.

3:00 pm Carnival in Trinidad” with Etienne Charles

Trinidad-born jazz trumpeter Etienne Charles will transport the audience to Carnival in Trinidad through a program that weaves together short films with a lecture. The program will delve into the experience of Carnival as a dialogue between the past and the present. Etienne will explore African-based musical elements and traditions, discuss the masquerading traditions and the meaning behind the costumes and characters, the brass band tradition, and the evolution of the steel pans.

4:30 pm Climate Justice Conversation” with Rev. Sekou and Rev. Mariama White-Hammond

Rev. Sekou and Rev. Mariama White Hammond will share their experiences and perspective on working for social and climate justice, highlighting the connection between arts, faith, and activism. Also present will be leaders of Springfield’s Climate Justice Initiative who will share the experience of Springfield residents and discuss efforts being made to move Springfield forward in addressing socio-economic and health disparities, while also addressing the issue of climate change.

Rev. Sekou’s music reflects the African American roots of American music through soul, funk, and gospel music. He delivers a rousing, spiritually moving, and politically charged performance that has been referred to as “one-part protest rally, one-part Pentecostal tent revival, and one-part late-night juke joint”. He speaks to these issues through the written and spoken word, as well as through music.

Reverend Mariama White-Hammond from the New Roots African Methodist Episcopal Church in Boston, and newly appointed Chief of Energy, Environment and Open Spaces for the City of Boston, is an activist and advocate for ecological and social justice, youth engagement, and Spirit-filled organizing. As former director of Project HIP-HOP (Highways Into the Past- History, Organizing, and Power), she used the arts as a tool to raise awareness for social issues from juvenile incarceration to funding for public transportation. She has received numerous awards including the Barr Fellowship, the Celtics Heroes Among Us, The Roxbury Founders Day Award, and the Boston NAACP Image award.

6:00 pm New Orleans Voodoo, Music, and Carnival Culture: The Background of Charles Neville

This lecture connects to the exhibition “Horn Man: The Life and Musical Legacy of Charles Neville” currently on display at the Springfield Wood Museum in collaboration with the Blues to Green Jazz and Roots Festival. Dr. Ina Fandrich, a cultural historian and Voodoo expert from New Orleans, will explore with us the colorful, magical, but also very violent and dangerous world in which Mr. Neville grew up.

The Grammy-award-winning saxophonist was born into a legendary family of musicians in a city that prides itself to be the birthplace of Jazz. In New Orleans, successful musicians like Charles and his three brothers, who founded together in 1977 the famous Neville Brothers Band, needed to be proficient in all local genres of music, and that they were to perfection, bringing every audience worldwide to their feet to dance.

Dr. Fandrich will introduce us to New Orleans’ rich black Carnival and African-based spiritual traditions that are at the center of much of the musical repertoire of the Neville Brothers.

Join us for a day full of music, pop-up food and beverage vendors, supporting local businesses, and an unforgettable family-friendly celebration.

If you are the after-party type, we have two awesome options for you! Head over to Theodore’s Booze, Blues, and BBQ or Dewey’s Jazz Lounge for incredible music, food and drinks, and more festival fun.

As in years prior, admission is always free to the Springfield Jazz & Roots Festival, but what is new this year is required RSVP-ing due to capacity limitations in our new space. It’s easy to RSVP just use the button below!


The Springfield Jazz & Roots Festival takes place on August 14, 2021 from 1-10PM in the streets surrounding Stearns Square, between Worthington and Bridge Streets.

Don’t let the rain deter you from coming to the festival. Grab your favorite umbrella and join us! If severe weather affects any part of the event, we will make announcements on-site, or you can check our social media for updates in real-time.

When parking for this event, we ask all attendees to use the TD flat lot and the Civic Center parking garage. Plan extra time for parking as these options may fill up!


August 14
1:00 pm - 10:00 pm EDT


Stearns Square
Stearns Square
Springfield, 01103 United States
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