A Note From Christine:

Hello!! The best plans usually start with someone saying, “Have you heard about this?” Consider this your weekly version of that. Grab a cup of coffee and let's get into it!

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Apparently the regular Big E cream puff wasn't enough.

The Big E opens September 18, and this year's food preview gave us a first look at what's coming … including a Peanut Butter Cream Puff Topped With Marshmallow Fluff.Yes. They did that!

There are plenty of New Foods at The Big E 2026 coming this year. So many new ones to try. I can’t wait!!!

The Taste of Northampton gives you the perfect opportunity to spend the day eating your way through Northampton, here it is. Restaurants, breweries, food vendors and specialty producers will be taking over downtown for two days, along with live music and plenty happening in between. I'd go hungry and make a day of it!

Saturday, September 12 | 11 AM–8 PM
Sunday, September 13 | 11 AM–6 PM

The Ashfield Lighted Boat Parade may be my favorite find of the week. A parade of illuminated artwork floating across a lake at dusk? I had no idea this existed.

There'll be live music, performers and food before the boats take to Ashfield Lake, and afterward you can get a closer look at the artwork and meet the artists who created it.

Saturday, September 12 | Parade at 7:30 PM | Ashfield

Glendi: Springfield’s Greek Festival

If Greek food is involved, you don't have to ask me twice. Springfield's annual Glendi Greek Festival is back for three days at St. George Greek Orthodox Cathedral with Greek food, live music and festivities. Admission is $2. That's an easy yes!

September 11–13 | Springfield

53rd Annual Mattoon Street Arts Festival

FREE ADMISSION - Celebrating Fifty-three years!! You know an event has become part of Western Mass when it's been around that long. More than 100 artists and exhibitors will line historic Mattoon Street Arts Festival this weekend, along with food vendors and strolling musicians.

And even if you don't need another piece of art, the setting itself is worth the walk. Mattoon Street and its beautiful Victorian row houses are one of those little pockets of Springfield you can easily forget are there.

Saturday, September 12 | 10 AM–5 PM
Sunday, September 13 | 10 AM–4 PM

Looking For More?

These are only a few things happening this weekend. You'll find live music, festivals, markets, family events and plenty more …

Okay, this one made me smile! The Biggest Tiny Art Show at the Mill District Local Art Gallery in North Amherst, they're creating an art show made entirely from canvases measuring just 2 inches by 2 inches.

But here's what makes it even better: you can add one yourself.

Stop in, they'll give you the tiny canvas, and you create whatever you want. It's free, your masterpiece becomes part of the exhibit, and donations to the Amherst Survival Center are encouraged.

The exhibit runs through October 11.

I'm an artist and they're handing out tiny canvases! Obviously, I'm going!!!

This one feels like it belongs in a movie!

Built in 1917, this Georgian Colonial still has the details that give an old house its soul — fireplaces, custom millwork, beautiful architecture and rooms that feel made for gathering. What I love is that it’s been brought into the present without stripping away the history.

And then there’s the property itself. Nearly seven private acres, a heated saltwater pool, spa, firepit, gazebo, English gardens, a wine cellar and even room for horses. I could easily picture a summer night out by that pool with friends and a bottle of wine.

This one feels like the best of both worlds: a house with history, but a life that feels completely modern.

If you’ve never been to The Student Prince, this is a good excuse to finally go. This Springfield landmark has been on Fort Street since 1935. It’s known for traditional German food, old-school charm and an incredible collection of beer steins. Walk through the door and you immediately feel the history. It’s one of those places that just feels special.

And Thursday night gives you another reason to go. Start with dinner inside, then head out to Fort Street for Fort Street Rocks. Brat Pack will be playing live from 6–9 PM as part of the Sommerfest Block Party and cancer-awareness fundraiser.

Dinner at a Springfield classic, live music outside and a good cause. That sounds like a pretty great Thursday night to me.

Thursday, September 10 | 6–9 PM | Springfield

There’s something about creating together that brings people together.

A Paint Social Art fundraiser turns supporting a cause you care about into a fun, social night out. Gather your friends, families, coworkers or community around something that matters to you. Then spend the evening laughing, painting and creating together all while raising money for your favorite organization.

Beginners are welcome! You are guided step by step to your completed painting and everyone goes home with their completed masterpiece. All the supplies are provided; making it easy to plan, organize and even more fun to attend!!

Have a fun night out at your next fundraiser, while creating great memories & masterpiece for a great cause!

Thursday, September 10 | 4:30–7:30 PM
The Landing | Springfield | FREE

Soul, funk, Motown and rock outside at The Landing. And it's free. That's a pretty easy Thursday-night plan.

Friday, September 11 | 9 PM
Theodore's Booze, Blues & BBQ | Springfield

Blues at Theodore's on a Friday night feels like one of those plans that doesn't need much explaining.

Thursday, September 10 | 7 PM
Iron Horse Music Hall | Northampton

Irish music meets Americana and bluegrass at the Iron Horse. If you've never heard JigJam, this may be a fun one to discover live.

This is just a taste of what's on the calendar this week.

Western Mass Insider reaches engaged readers who love connecting with and discovering local businesses, events, experiences, and things to do throughout the region.

If your business feels like a natural fit for our readers, I’d love to find a way to work together.

Until next time … keep exploring the Pioneer Valley

Curated with care by Christine Carbonaro-Freda westernmassinsider.com