The Best Fall Fairs & Festivals in Western and Central MA: September 2026 Guide

Sep 3

September in Massachusetts is basically our reward for surviving humidity.

Cooler nights are coming. The first leaves are changing. Apple cider donuts have returned to their rightful place in society.

And our local fair season is HERE.

If you're looking for things to do in Western Massachusetts or Central Massachusetts in September 2026, there are some pretty iconic events happening throughout the region.

Here are a few worth putting on your calendar.

Three County Fair | Northampton, MA

September 4–7, 2026

The Three County Fair has been a Western Massachusetts tradition for generations and takes over the fairgrounds in Northampton over Labor Day weekend.

Expect agricultural exhibits, animals, entertainment, food, competitions and classic fair activities.

If you're spending the day in Northampton, leave yourself some extra time to explore downtown too.

Spencer Fair | Spencer, MA

September 4–7, 2026

Heading toward Central Massachusetts?

The Spencer Fair is another Labor Day weekend tradition featuring agricultural exhibits, entertainment, food, competitions and plenty of classic New England fair energy.

It's also a great excuse to explore more of Worcester County if you're considering moving toward the Central Massachusetts side of my service area.

Sterling Fair | Sterling, MA

September 11–13, 2026

The Sterling Fair brings another traditional agricultural fair experience to Central Massachusetts.

For anyone who loves the smaller community fairs just as much as the massive ones, this deserves a spot on the September list.

The Big E | West Springfield, MA

September 18–October 4, 2026

Okay.

We can't talk about September in Western Massachusetts without talking about The Big E.

It's practically its own season around here.

The Eastern States Exposition brings together all six New England states for food, concerts, rides, agricultural exhibits, shopping and the famous Avenue of States.

And then there is Big E food.

You may arrive saying you're only going to have one thing.

That's adorable.

Plan accordingly.

Old Deerfield Fall Arts & Crafts Festival | Deerfield, MA

If your preferred version of fall involves handmade goods, historic New England scenery and approximately 400 things you suddenly NEED for your house, Deerfield belongs on your radar.

The annual fall arts and crafts festival brings artisans and visitors to historic Deerfield and is a completely different experience from the traditional agricultural fairs.

Why I Love September in Western Massachusetts

These events are fun, obviously.

But they're also part of what I love about living here.

Western and Central Massachusetts aren't just collections of towns on a map.

They're communities.

Our fairs, festivals, downtown events, farmers markets and local traditions are where you actually experience that.

And if you're considering moving here, I genuinely recommend attending them.

You'll learn more about an area walking around a community event for two hours than you ever will reading a list of statistics online.

Frequently Asked Questions

What are the best fairs in Western Massachusetts?

Some of the region's best-known fairs include The Big E in West Springfield and the Three County Fair in Northampton. Numerous smaller agricultural and community fairs also take place throughout Western Massachusetts each year.

When is The Big E 2026?

The Big E is scheduled for September 18 through October 4, 2026, at the Eastern States Exposition grounds in West Springfield.

Are there fairs in Central Massachusetts?

Yes. The Spencer Fair and Sterling Fair are two September traditions in Central Massachusetts, with additional festivals and community events happening throughout Worcester County.

Is September a good time to visit Western Massachusetts?

Absolutely. September brings cooler weather, fairs, festivals, orchards and the beginning of fall foliage season, making it one of the best months to explore the region.

Thinking About Living Here?

If you find yourself spending a September weekend here and thinking, "Wait... I could actually live here," we should probably talk. 😂

I help buyers relocate throughout Western Massachusetts, Central Massachusetts and northern Connecticut, and one of my favorite parts of my job is helping people understand the communities they're considering, not just the houses available in them.

Because where you live matters just as much as what you live in.

About Angie Schermerhorn

Angie Schermerhorn is a REALTOR® with the Stephanie Salerno Team at Coldwell Banker Realty serving Western Massachusetts, Central Massachusetts and northern Connecticut.

Angie helps buyers and sellers navigate real estate with a clear, personal and approachable process while also helping relocation clients understand what everyday life actually looks like throughout the communities she serves.

Angie Schermerhorn

I’m Angie Schermerhorn, a Western Massachusetts Realtor with the Stephanie Salerno Team at Coldwell Banker Realty, and I help first-time homebuyers and first-time sellers feel confident every step of the way.

Most of my clients are working moms, independent women, and LGBTQ+ buyers who are doing this for the first time, buying their first home, selling their first home, or stepping into their next chapter. My job is to make the process feel clear, not scary.

I break everything down in real language, advocate hard for my clients, and don’t believe in pressure, fluff, or fear-based tactics. You’ll always know what’s happening, what your options are, and what makes the most sense for you.

Outside of real estate, I’m all about community, good coffee, and a great glass of wine. I’ve lived in Western Massachusetts my whole life, and I truly love the towns I serve and the people who make them feel like home.

Buying or selling a home is a huge move financially and emotionally and I take that responsibility seriously. I’m here to guide you, protect you, and celebrate you when you get the keys (or the check!).

What truly sets me apart is how personal I make this experience. I don’t just open doors, I build real relationships. I stay accessible, I care deeply about what this move means for your life (not just your finances), and I support you long after the paperwork is signed. My clients know they can text me the “silly” questions, the big fears, and the excited wins and I’ll always show up. I always say, “Get ready to have a friend for life.”

If you’re thinking about buying or selling your first home in Western Massachusetts and want a Realtor who’s honest, down-to-earth, and truly in your corner, I’d love to help!