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.

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Old Sturbridge Village, The Sleepy Hollow Experience

November 3, 2019 @ 7:30 pm - 9:30 pm EST

|Recurring Event (See all)

An event every week that begins at 7:30 pm on Sunday, Wednesday, Thursday, Friday and Saturday, repeating until November 3, 2019

Through November 3. The Sleepy Hollow Experience returns again this month! At The Sleepy Hollow Experience, guests will be ghoulishly guided through the Village’s countryside where they will encounter Ichabod Crane, Katrina Van Tassel, Brom Bones and quite possibly the Headless Horseman.

Dates and shows are already selling out, reserve your spot today!

Please note that each outdoor performance is approximately 1.5 hours long, and requires standing and walking. Performances are rain or shine. If the evening is a rainout, a modified version of The Sleepy Hollow Experience will take place in Old Sturbridge Village’s Stephen M. Brewer Theater.

One and a half hours before show time, guests can enjoy hot soups and chowder, snacks and sweets. When you purchase your show tickets, you have the opportunity to pre-purchase a hearty soup/chowder meal for an additional $8. Additionally, sweets (and libations) will be available for purchase during intermission. Beer, wine, and cocktails will be available before the show and during intermission. You must have a valid photo ID in order to purchase any alcohol. Guests are welcome to enjoy their libations during the performance.

Learn More
BUY TICKETS

Times: Shows begin at 7:30 pm on Wednesday nights and 7:30 pm and 9:30 pm Thursday – Sunday

The Sleepy Hollow Experience at Old Sturbridge Village

5 Slightly Spooky Historical Fun Facts

“Jack-o-lanterns” comes from Irish folklore about a man named Stingy Jack in the 1500s. The Irish story mixed with another tradition of making lanterns out of vegetables like turnips or beets to celebrate the harvest. In the mid-1800s, Stingy Jack’s name was attached to the pumpkin lanterns.

Today, the Legend of Sleepy Hollow often evokes thoughts of Halloween. Somewhat ironically, however, Washington Irving’s story never mentions Halloween.

The headless horseman in the Legend of Sleepy Hollow is supposedly a soldier who was decapitated in an unnamed American Revolutionary War battle. There are other stories of a Headless Horseman around the world as well, most notably a German story that predates “The Legend of Sleepy Hollow.”

The story of how Halloween came to be is not entirely clear or straightforward. It has its roots in a murky blend of pagan and Christian beliefs and folk customs from England, Ireland, Scotland and continental Europe. Many historians see the origin of Halloween in the pre-Christian Celtic festival of Samhain.

Halloween was practically unknown in early 19th-century New England, but that would change quickly. By the 1860s it was not uncommon for boys to play pranks, or girls to toy with romantic fortune telling on Halloween. By the end of the 19th century, costumed Halloween balls for adults were on the rise among the socially elite.

Details

Date:
November 3, 2019
Time:
7:30 pm - 9:30 pm
EST
Website:
www.osv.org/event/sleepy-hollow/

Venue

Old Sturbridge Village
1 Old Sturbridge Village Road
Sturbridge, MA 01566
+ Google Map
Phone:
(800) 733-1830
Website:
www.osv.org