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.

springfieldthunderbirds.com

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.

Connecticut Trolley Museum, Want to be a Motorman?

Connecticut Trolley Museum 58 North Road, East Windsor

This is your chance to get behind a controller and operate a trolley under the guidance of an instructor. This program is a shortened version of the Guest Motorman Experience. Participation in operating our historic trolleys is limited to adults only (18+). Admission to the museum is included with the cost of the event. Tickets must […]

Connecticut Trolley Museum, Father’s Day

Connecticut Trolley Museum 58 North Road, East Windsor

The Connecticut Trolley Museum is excited to honor Fathers and Grandfathers half-price admission with a paid adult or child admission. "Behind-the-Scenes” tour will give visitors the opportunity to take a close-up look at some of the current restoration projects including Connecticut Company Car #3001 (almost 120 years old!), Brooklyn Rapid Transit #169 (127 years old!) […]

Connecticut Trolley Museum, Fire Truck Show

Connecticut Trolley Museum 58 North Road, East Windsor

Fire Truck Show & First Responders Day- The event will give visitors the opportunity to get up close and personal with all aspects of the firefighting industry including over twenty First Responder Vehicles. During your visit you will also learn more about the Fire Truck Museum’s (housed on the same grounds of the Trolley Museum) […]

Connecticut Trolley Museum, Connecticut Open House Day

Connecticut Trolley Museum 58 North Road, East Windsor

The Connecticut Trolley Museum will participate in the 17th Annual Connecticut Open House Day – a unified celebration of the State’s fascinating world of art, history, and tourism – on June 12th, 2021. During this one-day event, CT Trolley Museum, along with more than 200 other organizations and attractions throughout the state, will open its […]

Connecticut Trolley Museum, Beer and Wine Tasting

Connecticut Trolley Museum 58 North Road, East Windsor

Sample wine and beer from local wineries & breweries while enjoying all the Museum has to offer! New Earth and Aquadutes will be performing throughout the day. Cost will be $20 per person which will cover admission to the museum and the tastings. You must be 21 to drink and will have to show your […]

Connecticut Trolley Museum, Mother’s Day

Connecticut Trolley Museum 58 North Road, East Windsor

The Connecticut Trolley Museum is excited to honor Mothers and Grandmothers free admission with a paid adult or child admission. Spend a few hours with the family, enjoying all the activities at the trolley museum. Inside the Visitor Center is a train table for the little ones, coloring activities, and a dress up station! All activities and […]

Recurring

Connecticut Trolley Museum, Easter Eggspress

Connecticut Trolley Museum 58 North Road, East Windsor

Motorwoman Cotton-Tail will be roaming the grounds and posing for pictures distantly from 11am-3pm.  Each child will receive an Easter egg with a surprise inside when they complete a Scavenger Hunt, make a Bunny Ear Craft & visit the Fire Truck Museum.  Earn up to three filled eggs! Take a trolley ride operated by period […]

Recurring

Connecticut Trolley Museum, Easter Eggspress

Connecticut Trolley Museum 58 North Road, East Windsor

Motorwoman Cotton-Tail will be roaming the grounds and posing for pictures distantly from 11am-3pm.  Each child will receive an Easter egg with a surprise inside when they complete a Scavenger Hunt, make a Bunny Ear Craft & visit the Fire Truck Museum.  Earn up to three filled eggs! Take a trolley ride operated by period […]

Recurring

Connecticut Trolley Museum, Easter Eggspress

Connecticut Trolley Museum 58 North Road, East Windsor

The Connecticut Trolley Museum presents Easter Eggspress on March 27th, 28th & April 2nd & 3rd. Motorwoman Cotton-Tail will be roaming the grounds and posing for pictures distantly from 11am-3pm.  Each child will receive an Easter egg with a surprise inside when they complete a Scavenger Hunt, make a Bunny Ear Craft & visit the […]

Recurring

Connecticut Trolley Museum, Easter Eggspress

Connecticut Trolley Museum 58 North Road, East Windsor

The Connecticut Trolley Museum presents Easter Eggspress on March 27th, 28th & April 2nd & 3rd. Motorwoman Cotton-Tail will be roaming the grounds and posing for pictures distantly from 11am-3pm.  Each child will receive an Easter egg with a surprise inside when they complete a Scavenger Hunt, make a Bunny Ear Craft & visit the […]

Recurring

Connecticut Trolley Museum, Winterfest and “The Tunnel of Lights”

Connecticut Trolley Museum 58 North Road, East Windsor

LAST WEEK!!  Open every day until Dec 30. Join hundreds of others and start a family tradition of coming for a trolley ride during the holiday season. Whether you ride a closed car or brave the cold to ride the open "electric sleigh", we promise you a good time and one that you'll remember for […]

Recurring

Connecticut Trolley Museum, Winterfest and “The Tunnel of Lights”

Connecticut Trolley Museum 58 North Road, East Windsor

LAST WEEK!!  Open every day until Dec 30. Join hundreds of others and start a family tradition of coming for a trolley ride during the holiday season. Whether you ride a closed car or brave the cold to ride the open "electric sleigh", we promise you a good time and one that you'll remember for […]

Recurring

Connecticut Trolley Museum, Winterfest and “The Tunnel of Lights”

Connecticut Trolley Museum 58 North Road, East Windsor

LAST WEEK!!  Open every day until Dec 30. Join hundreds of others and start a family tradition of coming for a trolley ride during the holiday season. Whether you ride a closed car or brave the cold to ride the open "electric sleigh", we promise you a good time and one that you'll remember for […]

Recurring

Connecticut Trolley Museum, Winterfest and “The Tunnel of Lights”

Connecticut Trolley Museum 58 North Road, East Windsor

LAST WEEK!!  Open every day until Dec 30. Join hundreds of others and start a family tradition of coming for a trolley ride during the holiday season. Whether you ride a closed car or brave the cold to ride the open "electric sleigh", we promise you a good time and one that you'll remember for […]

Recurring

Connecticut Trolley Museum, Winterfest and “The Tunnel of Lights”

Connecticut Trolley Museum 58 North Road, East Windsor

LAST WEEK!!  Open every day until Dec 30. Join hundreds of others and start a family tradition of coming for a trolley ride during the holiday season. Whether you ride a closed car or brave the cold to ride the open "electric sleigh", we promise you a good time and one that you'll remember for […]

Recurring

Connecticut Trolley Museum, Storytime Trolley with Santa & Elf

Connecticut Trolley Museum 58 North Road, East Windsor

Storytime trolley with Santa & Elf will run on Saturday and Sunday Dec 12th & 13th. Visitors will enjoy a ride in a decorated vintage trolley car where Santa will visit with each child (distantly). Also, while on board Santa’s elf will read a holiday story and each child will complete a holiday craft. Following […]

Recurring

Connecticut Trolley Museum, Storytime Trolley with Santa & Elf

Connecticut Trolley Museum 58 North Road, East Windsor

Storytime trolley with Santa & Elf will run on Saturday and Sunday Dec 12th & 13th. Visitors will enjoy a ride in a decorated vintage trolley car where Santa will visit with each child (distantly). Also, while on board Santa’s elf will read a holiday story and each child will complete a holiday craft. Following […]

Recurring

Connecticut Trolley Museum, Christmas Tree Trolley

Connecticut Trolley Museum 58 North Road, East Windsor

Christmas Tree Trolley will held on Saturday & Sunday November 28th & 29th. For that special authentic Christmas experience, travel by an antique trolley car to Skylark Place where you can choose a specialty selected pre-cut white spruce tree and bring it back with you on the trolley. Additionally, enjoy the Visitor Center which is decorated […]

Recurring

Connecticut Trolley Museum, Christmas Tree Trolley

Connecticut Trolley Museum 58 North Road, East Windsor

Christmas Tree Trolley will held on Saturday & Sunday November 28th & 29th. For that special authentic Christmas experience, travel by an antique trolley car to Skylark Place where you can choose a specialty selected pre-cut white spruce tree and bring it back with you on the trolley. Additionally, enjoy the Visitor Center which is decorated […]