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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Connecticut Trolley Museum

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58 North Road
East Windsor, CT 06088
(860) 627-6540 www.ct-trolley.org

The Connecticut Trolley Museum, founded in 1940, is the oldest incorporated museum in the United States dedicated to the electric railroad. View an historic collection of over 70 pieces of trolley and railroading history dating back to 1869. The Visitor Center offers numerous education exhibits that show the history of trolley transportation. Experience a three-mile round trip antique trolley car ride that takes you back in time.

During your visit, you can see historic passenger and freight street “trolley” cars, interurban cars, elevated railway cars, passenger and freight railroad cars, service cars, locomotives, and a variety of other equipment from railways around Connecticut. You will also find examples from Brooklyn, Boston, New Orleans, Milwaukee, Cleveland, Springfield, Lynchburg, Montreal, and even Rio De Janeiro, Brazil.

Connecticut Trolley Museum

The Connecticut Trolley Museum is located at 58 North Road (Rt. 140) and is a short 15 minutes north of Hartford or a short 15 minutes south of Springfield. Admission prices are $10 for Adults, $9 for Seniors (62+), Children (ages 4-12) $7, children (ages 3 & under) and Museum Members free. For more information, visit ct-trolley.org or call (860) 627-6540.

From Springfield and Points North

Take I-91 south from Massachusetts into Connecticut. Take Exit 45 for State Route 140, Ellington, and Warehouse Point. At the bottom of the ramp, turn left heading under the highway. Stay straight on Route 140 (East). The Museum will be on the right about 1 mile from the highway after the third traffic light.

From Hartford and Points South

Take I-91 north from Hartford. Take Exit 45 for State Route 140, Warehouse Point, and Ellington. At the bottom of the ramp turn right and stay straight on Route 140 (East). The Museum will be on the right about 1 mile from the highway after the second traffic light.

Montreal Tramways 4
Springfield Electric Railway 16
Fair Haven & Westville Railroad Co. 355
New Orleans Public Service 836
Connecticut Company 1326
Montreal Tramways 2600
Boston Elevated Railway 5645

July 2020

Connecticut Trolley Museum, Storytime

July 16 @ 10:00 am - 11:00 am EDT
|Recurring Event (See all)

An event every week that begins at 10:00 am on Thursday and Friday, repeating until July 17, 2020

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

Stories come alive for children when they are read to aloud aboard our vintage operating trolleys. Every Thursday and Friday throughout the summer hop aboard the Storytime Trolley, featuring stories about the adventures of trolleys and trains. The reading will be inside one of our historic trolleys and a trolley ride will follow. Every story is different and all ages are welcome! Storytime is included with admission. Make sure to arrive early to get your tickets as the Storytime Trolley…

Find out more »

Connecticut Trolley Museum, Storytime

July 17 @ 10:00 am - 11:00 am EDT
|Recurring Event (See all)

An event every week that begins at 10:00 am on Thursday and Friday, repeating until July 17, 2020

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

Stories come alive for children when they are read to aloud aboard our vintage operating trolleys. Every Thursday and Friday throughout the summer hop aboard the Storytime Trolley, featuring stories about the adventures of trolleys and trains. The reading will be inside one of our historic trolleys and a trolley ride will follow. Every story is different and all ages are welcome! Storytime is included with admission. Make sure to arrive early to get your tickets as the Storytime Trolley…

Find out more »

Connecticut Trolley Museum, Summer Music Series

July 17 @ 5:30 pm - 8:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Friday, repeating until July 31, 2020

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

The Connecticut Trolley Museum has re-opened part-time and is kicking off its Summer Music Series during the month of July. The Museum will be hosting live music in the courtyard on Friday Nights in July- The Schedule is as follows: July 17th- New Earth July 24th The Aquatudes July 31st Just Jeannie A Trolley ride is included with your admission ticket. Everyone will be practicing social distancing and the Museum will have designated marked areas for you to enjoy the…

Find out more »

Connecticut Trolley Museum, Summer Music Series

July 24 @ 5:30 pm - 8:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Friday, repeating until July 31, 2020

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

The Connecticut Trolley Museum has re-opened part-time and is kicking off its Summer Music Series during the month of July. The Museum will be hosting live music in the courtyard on Friday Nights in July- The Schedule is as follows: July 17th- New Earth July 24th The Aquatudes July 31st Just Jeannie A Trolley ride is included with your admission ticket. Everyone will be practicing social distancing and the Museum will have designated marked areas for you to enjoy the…

Find out more »

Connecticut Trolley Museum, Summer Music Series

July 31 @ 5:30 pm - 8:00 pm EDT
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Friday, repeating until July 31, 2020

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

The Connecticut Trolley Museum has re-opened part-time and is kicking off its Summer Music Series during the month of July. The Museum will be hosting live music in the courtyard on Friday Nights in July- The Schedule is as follows: July 17th- New Earth July 24th The Aquatudes July 31st Just Jeannie A Trolley ride is included with your admission ticket. Everyone will be practicing social distancing and the Museum will have designated marked areas for you to enjoy the…

Find out more »

August 2020

Connecticut Trolley Museum, Super Hero and Princess Day

August 22 @ 11:00 am - 3:00 pm EDT
Connecticut Trolley Museum, 58 North Road
East Windsor, CT 06088
+ Google Map

Dress up as your favorite Super Hero or Princess and join us for a fun memorable day. It is sure to be a SUPER time! Additionally, take as many trolley rides as you would like operated by period dressed motormen. Learn historic information about each car you ride and how the museum began. Inside the Visitor Center you will find more trolley cars, artifacts and a gift shop to buy that 'special' souvenir. On the same grounds is the Connecticut Fire Truck…

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May 2021

Connecticut Trolley Museum, Mother’s Day

May 9, 2021 @ 10:00 am - 4:30 pm EDT
Connecticut Trolley Museum, 58 North Road
East Windsor, CT 06088
+ Google Map

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 Fire Truck Museum entrance is included with your admission price.

Find out more »

June 2021

Connecticut Trolley Museum, 80th Anniversary Celebration

June 26, 2021 @ 10:00 am - 4:30 pm EDT
Connecticut Trolley Museum, 58 North Road
East Windsor, CT 06088
+ Google Map

Come celebrate 80 years with us!

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