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, 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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October 2020

Zoar Outdoor, Family Float Trip

October 2
|Recurring Event (See all)

An event every week that begins at 12:00 am on Thursday, Friday and Saturday, repeating until October 11, 2020

Zoar Outdoor, 7 Main St
Charlemont, MA 01339
+ Google Map

Our half-day guided Float Trip is the perfect introduction to rafting for folks who want to dip a toe in the water before taking on our Zoar Gap trip or for groups with children as young as 5 years old. Our Family Float trip showcases the beauty of the Deerfield River as it meanders through farmland and the rolling Berkshire foothills along the historic Mohawk Trail. Our professional river guides provide insight into the natural and cultural history of the…

Find out more »

Abandoned Building Brewery, Outdoor Patio Beer Garden

October 2
|Recurring Event (See all)

An event every week that begins at 12:00 am on Thursday, Friday and Saturday, repeating until October 31, 2020

Abandoned Building Brewery, 142 Pleasant St
Easthampton, MA 01027
+ Google Map

We've been so happy to see your faces in person...from a distance. Our outdoor patio seating area is open in the parking lot right behind the brewery. We will continue to offer safe outdoor seating with table service and local food trucks every week. Our updated hours are now Thursday from 5 to 8, Friday from 4-8, and Saturday from 2-7 pm. October is the last month we will be offering outdoor seating! October 1st: Caravan Kitchen October 2nd: TBD…

Find out more »

The Log Cabin, Big E Craft Pub

October 2
|Recurring Event (See all)

An event every week that begins at 12:00 am on Sunday, Thursday, Friday and Saturday, repeating until October 18, 2020

The Log Cabin Banquet and Meeting House, 500 Easthampton Road
Holyoke, MA 01040
+ Google Map

Every Thursday, Friday, Saturday, and Sunday through October 18th, the New England Craft Pub normally located at the Big E will be at the Log Cabin! This Big E Favorite will feature at least 18 regional beers and ciders on tap, outdoor live entertainment (weather permitting), and of course our Big E inspired food, like the famous Turducken Sandwich, Mick’s Irish Nachos, our signature Chicken Pot Pie and the well known Big E Cream Puff. Indoor and outdoor tables with…

Find out more »

The Big E Food-To-Go Drive-Thru

October 2
|Recurring Event (See all)

An event every week that begins at 12:00 am on Sunday, Tuesday, Wednesday, Thursday, Friday and Saturday, repeating until October 18, 2020

Eastern States Exposition, 1305 Memorial Avenue
West Springfield, MA 01089
+ Google Map

The Big E Food-To-Go Drive-Thru, sponsored by Westfield Bank, will feature three different vendors each week who will bring their authentic and iconic Big E foods to the Eastern States Exposition Fairgrounds! Drive-Thru dates are September 22 - 27, September. 29 - October 4, October 6 -11, and October 13 - 18. Hours are Tuesdays to Thursdays from 11AM - 7PM, Fridays from 10AM - 8PM and Saturdays & Sundays from 9AM - 7PM. Week #2 Vendors (Sept. 29 - Oct. 4,…

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Nomads Adventure Quest, OPEN!!

October 2 - October 4
Nomads Adventure Quest, 100 Bidwell Road
South Windsor, CT 06074
+ Google Map

The wait is over. Nomads is officially OPEN and ready for you to get back to ADVENTURE. Nomads offers Laser Tag, Bumper Cars, Black Light Mini Golf, Route 66 Bowling, Spinning Teacups, over 100 Arcade Games, and 2 Full Size Basketball Courts. Please come and join us for some fun. Please bring masks for the safety of our guests. Bounce Houses, Rock Wall, Virtual Reality, Axe Throwing and Red’s Tavern will remain closed. Friday: 4pm to 10pm Saturday: 12pm to 10pm ​Sunday: 12pm to…

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Sonny’s Place, Harvest Happenings

October 2
|Recurring Event (See all)

An event every week that begins at 12:00 am on Sunday, Friday and Saturday, repeating until November 1, 2020

Sonny’s Place, 349 Main Street (Route 190)
Somers, CT 06071
+ Google Map

CELEBRATE FALL AT SONNY’S PLACE! Enjoy special attractions and activities along with a full menu of delicious seasonal food and drinks! Halloween music is in the air and sets the mood across the park. Play a round of Pumpkin Mini Golf and see the hundreds of hand carved (and lit at night) pumpkins around the course. Special Attractions Pumpkin Mini Golf– Enjoy our miniature golf course, with a twist! While golfing, you’ll be able to see around 500 hand carved…

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Sunderland, Mike’s Maze at Warner Farm

October 2 @ 9:00 am - 5:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 9:00 am on Sunday, Friday and Saturday, repeating until November 1, 2020

Warner Farm, 23 S. Main Street
Sunderland, MA 01375
+ Google Map

VOTE! The stalks have never been higher... One hundred years ago today in 1920, the decades-long battle for women’s suffrage was finally realized with the passing of the 19th amendment. And fifty-five years ago, on August 6, the Voting Rights Act of 1965 was passed, prohibiting racial discrimination in voting. We’ve designed 8-acres of campaign trails in honor of these landmark achievements in our country’s history. From straw polls to donut holes, we invite you to celebrate democracy—socially-distanced—at Mike’s Maze…

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Connecticut Trolley Museum, Pumpkin Patch

October 2 @ 10:00 am - 5:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 10:00 am on Sunday, Thursday, Friday and Saturday, repeating until October 31, 2020

Connecticut Trolley Museum, 58 North Road
East Windsor, CT 06088
+ Google Map

Pumpkin Patch is a family fun filled adventure where you ride on a trolley car out to the pumpkin patch and children can pick out a FREE sugar-sized pumpkin. Each child will get a bag filled with stickers to decorate their pumpkin and the arts and crafts tables will be open for the enjoyment of visitors. Don't forget you can take as many trolley rides as you would like. The Visitor Center will be open and decorated for Halloween. The Fire…

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The Springfield Armory, Walking Tour

October 2 @ 11:00 am - 12:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 11:00 am on Friday, repeating until October 9, 2020

The Springfield Armory National Historic Site, One Armory Square, Suite 2
Springfield, MA 01105
+ Google Map

The Springfield Armory National Historic Site, in coordination with Springfield Technical Community College, will be offering ranger guided tours of the historic grounds on Fridays at 11:00 a.m., weather permitting. Registration is limited to no more than 10 people total including staff. You must have proof of registration to enter the grounds. You will received a confirmation email with instructions and an attestation form that you must complete and show for entrance to the Springfield Technical Community College grounds for…

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The Student Prince Restaurant, Oktoberfest

October 2 @ 6:00 pm - 9:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 6:00 pm on Friday and Saturday, repeating until October 31, 2020

The Student Prince Restaurant, 8 Fort Street
Springfield, MA 01103
+ Google Map

Roll out the barrel because Springfield’s Original Mighty Oktoberfest is going to be a barrel of fun every weekend in October on Fort Street in downtown Springfield. It’s the area’s largest, wildest and most authentic Oktoberfest in all of Western Mass!  

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The Log Cabin, Bites & Bottles

October 2 @ 6:00 pm - 9:00 pm EDT
The Log Cabin Banquet and Meeting House, 500 Easthampton Road
Holyoke, MA 01040
+ Google Map

Join us as we continue our Friday night wine dinners with various bites and bottles to enjoy! Amazing Food! Amazing Wine! Amazing Views! All with Live Music! First Course: Ahi Tuna, Jasmine Rice, Seaweed, Sweet Asian Glaze Paired with ACK Rose Second Course: Jerk Chicken Thighs, Smoky grits, Corn Relish Paired with Martin Codax Albarino Third Course: Braised Angus Short Ribs, Root Vegetables and Sweet Potato Mashed Paired with Cline Cellars Syrah Fourth Course: Peanut Butter Fudge Cheesecake Paired with…

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Springfield Museums, Exhibits

October 3 - November 1
Springfield Museums, 21 Edwards Street
Springfield, MA 01103
+ Google Map

Chance Encounters - Mixed Media Constructions by Shawn Farley; through March 7. 2021 Voices of Resilience: The Intersection of Women on the Move; Extended to January 3, 2021. The Outwin: American Portraiture Today; through April 4, 2021. Voices of Resilience: The Intersection of Women on the Move; through Jan 3 2021. Voices of Resilience celebrates the intersecting lives of women in Massachusetts and beyond who have changed the course of history. Through highlights of diverse ‘hidden figures’ and narratives, this exhibition explores the…

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Deerfield Memorial Hall Museum, Open

October 3 - October 31
Memorial Hall Museum, 10 Memorial St
Deerfield, MA 01342
+ Google Map

Come explore the museum’s 19 rooms of art, culture and history! We are located in the village of Deerfield, Massachusetts, but as the earliest historical society in the region, people from throughout Franklin County—as well as Hampshire and Hampden counties—entrusted their family stories to the Pocumtuck Valley Memorial Association. From fossils of dinosaur tracks to 20th century artifacts, this extraordinary collection continues to be enhanced by both donations and purchases. CURRENT SPECIAL EXHIBITS Fabric of Time New England History Told…

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Berkshire East, Thunder Mountain Bike Park

October 3
|Recurring Event (See all)

An event every week that begins at 12:00 am on Sunday, Monday, Friday and Saturday, repeating until October 31, 2020

Berkshire East Mountain Resort, 66 Thunder Mountain Road
Charlemont, MA 01339
+ Google Map

Thunder Mountain Bike Park is a gravity-fed park. You take the lift up and ride down the mountain. This style of riding is best suited for very specific bicycles and gear. If you don’t own this specific gear, we can provide you with a DH bike and all of the protective equipment at our full service rental shop. Fall: September 8th – October 31st Weekends 9:00am - 5:00pm Monday & Friday 10:00am - 5:00pm Closed Tuesday, Wednesday & Thursday Bring Your Bike

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Sonny’s Place, Weekend Happenings

October 3 - October 4
Sonny’s Place, 349 Main Street (Route 190)
Somers, CT 06071
+ Google Map

Live Acoustic- BONUS WEEKEND! Join us this Saturday and Sunday at the Pavilions Restaurant for a bonus weekend of Live Acoustic Music: 10/3-Dave Brunette- 6pm-9pm 10/3- Kevin Crane- 3pm-6pm Pavilions Restaurant Join us at the Pavilions Restaurant for our delicious, from scratch menu! On top of our regular menu, you can enjoy some great seasonal food and drink specials. The Pavilions Restaurant is open Wednesday- Sunday. Pavilions Menu

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Zoar Outdoor, Whitewater

October 3
Zoar Outdoor, 7 Main St
Charlemont, MA 01339
+ Google Map

Experience Class IV rafting excitement close to home on the Deerfield River’s most exciting section, the Monroe Bridge Dryway. Combining the rush of advanced whitewater, the beauty of the northern Berkshires and the camaraderie of a paddling adventure Full Day: Includes refreshing riverside snack and a full post-trip barbeque back at base. All Dryway trips meet at our base in Charlemont, Massachusetts Due to the current health crisis we are offering private trips set with a minimum and maximum group…

Find out more »

Zoar Outdoor, Family Float Trip

October 3
|Recurring Event (See all)

An event every week that begins at 12:00 am on Thursday, Friday and Saturday, repeating until October 11, 2020

Zoar Outdoor, 7 Main St
Charlemont, MA 01339
+ Google Map

Our half-day guided Float Trip is the perfect introduction to rafting for folks who want to dip a toe in the water before taking on our Zoar Gap trip or for groups with children as young as 5 years old. Our Family Float trip showcases the beauty of the Deerfield River as it meanders through farmland and the rolling Berkshire foothills along the historic Mohawk Trail. Our professional river guides provide insight into the natural and cultural history of the…

Find out more »

Abandoned Building Brewery, Outdoor Patio Beer Garden

October 3
|Recurring Event (See all)

An event every week that begins at 12:00 am on Thursday, Friday and Saturday, repeating until October 31, 2020

Abandoned Building Brewery, 142 Pleasant St
Easthampton, MA 01027
+ Google Map

We've been so happy to see your faces in person...from a distance. Our outdoor patio seating area is open in the parking lot right behind the brewery. We will continue to offer safe outdoor seating with table service and local food trucks every week. Our updated hours are now Thursday from 5 to 8, Friday from 4-8, and Saturday from 2-7 pm. October is the last month we will be offering outdoor seating! October 1st: Caravan Kitchen October 2nd: TBD…

Find out more »

The Log Cabin, Big E Craft Pub

October 3
|Recurring Event (See all)

An event every week that begins at 12:00 am on Sunday, Thursday, Friday and Saturday, repeating until October 18, 2020

The Log Cabin Banquet and Meeting House, 500 Easthampton Road
Holyoke, MA 01040
+ Google Map

Every Thursday, Friday, Saturday, and Sunday through October 18th, the New England Craft Pub normally located at the Big E will be at the Log Cabin! This Big E Favorite will feature at least 18 regional beers and ciders on tap, outdoor live entertainment (weather permitting), and of course our Big E inspired food, like the famous Turducken Sandwich, Mick’s Irish Nachos, our signature Chicken Pot Pie and the well known Big E Cream Puff. Indoor and outdoor tables with…

Find out more »

The Big E Food-To-Go Drive-Thru

October 3
|Recurring Event (See all)

An event every week that begins at 12:00 am on Sunday, Tuesday, Wednesday, Thursday, Friday and Saturday, repeating until October 18, 2020

Eastern States Exposition, 1305 Memorial Avenue
West Springfield, MA 01089
+ Google Map

The Big E Food-To-Go Drive-Thru, sponsored by Westfield Bank, will feature three different vendors each week who will bring their authentic and iconic Big E foods to the Eastern States Exposition Fairgrounds! Drive-Thru dates are September 22 - 27, September. 29 - October 4, October 6 -11, and October 13 - 18. Hours are Tuesdays to Thursdays from 11AM - 7PM, Fridays from 10AM - 8PM and Saturdays & Sundays from 9AM - 7PM. Week #2 Vendors (Sept. 29 - Oct. 4,…

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