Helping people make smart moves in Western Massachusetts and Northwestern Connecticut

There is a point every August when summer in Western Massachusetts starts to feel just a little bit different.

The days are still hot, nobody is ready to talk about putting away the patio furniture, and technically fall is still more than a month away. But the fairs start popping up. There are tractor pulls and livestock barns, fried dough and craft tents, midway rides, farm days and eventually, of course, The Big E.

Fair season has arrived.

If you live in Western Massachusetts or Northern Connecticut, you can pretty much find something to do every weekend from now well into October. Some of these are traditional agricultural fairs that have been around for generations. Others are community festivals, open farm days, arts festivals, and local celebrations that seem to belong in the same category.

So, rather than making you hunt them all down, I did it for you.

Here is my 2026 guide to fair season in Western Massachusetts and Northern Connecticut.

Littleville Fair — Chester, MA

August 7–9, 2026

We’re already a little late for this one, but I’m including it because the Littleville Fair really does help kick off fair season in our corner of Massachusetts.

The 104th Littleville Fair featured the kind of things you want from an old-fashioned country fair: oxen and truck pulls, a petting zoo, exhibits, line dancing, food and family activities.

If you missed it, put it on the calendar for next August.

Where: Littleville Fairgrounds, 15 Kinnebrook Road, Chester

Southwick Open Farm Day — Southwick, MA

Sunday, August 16, 2026 | 10 a.m.–4 p.m.

This isn’t technically a fair, but I’m including it anyway because it belongs here.

Southwick’s fourth annual Open Farm Day gives you a chance to travel around town visiting local farms, get a behind-the-scenes look at their operations, and learn a little more about the people who are still actively farming here.

And Southwick has a richer agricultural history than many people realize.

The event was created to connect residents with local farmers and recognize the role agriculture still plays in the community, from producing food and other goods to preserving some of the open space that makes Southwick look and feel like Southwick.

Pick up a passport at any participating location and use the included map to make your way around town.

Admission: Free, although some individual activities may have a modest charge.

Westfield Fair — Westfield, MA

August 21–23, 2026

This one is home turf for me.

The 98th Westfield Fair is a traditional agricultural fair held at the fairgrounds on Russellville Road. It’s the kind of local event that has managed to survive while so much around us has changed.

There are livestock and agricultural exhibits, a midway, craft barn, farm museum, petting zoo, live music, tractor and truck pulls, horse and oxen draws, kids’ activities and even a demolition derby.

For those of us who live in Westfield, it’s also one of those annual markers that tells you summer is beginning to wind down.

Where: Westfield Fairgrounds, 137 Russellville Road, Westfield

Heath Fair — Heath, MA

August 21–23, 2026

If you’re willing to take a ride toward Franklin County, the Heath Fair is serious country-fair territory.

Think antique tractors, truck and lawn tractor pulls, horse and oxen draws, sheep, rabbits, cattle, dairy goats, agricultural exhibits, local arts and crafts, live music, square dancing and horse-drawn wagon rides.

One useful warning straight from the organizers: cell service at the fairgrounds can be limited, and there is no ATM. Plan accordingly.

Cummington Fair — Cummington, MA

August 27–30, 2026

The Cummington Fair takes us into the final weekend of August and is another classic Western Massachusetts agricultural fair.

If your definition of a proper New England fair involves animals, agricultural competitions, entertainment, rides, fair food, and things being pulled by tractors, you’re in the right place.

Cummington is a bit of a drive from the Springfield/Westfield area, but it’s also a beautiful part of Western Massachusetts and makes an easy excuse for a late-summer day trip.

Southwick 250th Anniversary Celebration & Fireworks — Southwick, MA

Saturday, August 29, 2026

Southwick is celebrating America’s 250th anniversary with a parade, community celebration and — yes — fireworks.

The parade lines up at Southwick Regional High School at 3 p.m. and steps off at 4 p.m., traveling along Feeding Hills Road and Powder Mill Road to Whalley Park.

Beginning at 5 p.m., the evening celebration gets underway with food trucks, family activities and live music from 91 South.

Then, at dusk, fireworks.

This obviously isn’t an agricultural fair, but a hometown parade, food trucks, live music and fireworks on a late-August Saturday feels like it belongs in this guide.

Parade: 4 p.m.
Celebration: 5 p.m.
Fireworks: Dusk
Where: Whalley Park, 30 Powder Mill Road, Southwick

Blandford Fair — Blandford, MA

September 4–7, 2026

Labor Day weekend is when fair season really gets busy.

The Blandford Fair is close enough to Westfield to make this an easy outing and has been part of the town’s Labor Day weekend tradition for generations.

Expect the traditional mix of agricultural exhibits, animals, entertainment, competitions, food and family activities — with the decidedly small-town feel that separates these fairs from the giant ones.

Three County Fair — Northampton, MA

September 4–7, 2026

If you want something bigger for Labor Day weekend, head north to Northampton.

The Three County Fair represents Hampshire, Franklin and Hampden counties and combines its agricultural roots with the larger midway-and-entertainment experience.

It’s one of those Western Massachusetts traditions that has been around for generations, with agricultural exhibits, livestock, entertainment, rides and plenty of fair food.

Where: 54 Fair Street, Northampton

Wapping Fair — South Windsor, CT

September 10–13, 2026

Crossing the state line, the Wapping Fair gives Northern Connecticut its turn.

The 2026 fair includes agricultural, culinary, and craft exhibitions, live entertainment, tractor pulling, and a midway. It’s another good option if you’re looking for the traditional fair experience without traveling too far from the Massachusetts line.

Where: John J. Mitchell Fairgrounds, 75 Brookfield Street, South Windsor

Franklin County Fair — Greenfield, MA

September 10–13, 2026

The Franklin County Fair has been a Greenfield tradition for generations and brings another full-scale agricultural fair to the September calendar.

It’s farther north than most of the events on this list, but for people who love the traditional New England fair experience, it belongs on the guide.

Granby Open Farm Day — Granby, CT

Saturday, September 12, 2026

Granby describes Open Farm Day as feeling like a town-wide fair, which is good enough for me.

Farms throughout Granby open their doors for demonstrations, farm-fresh food, games, activities and opportunities to meet the animals and learn about the farms operating right here in the Farmington Valley.

It’s free, family-friendly, and a particularly good way to explore Granby beyond the places you see driving along the main roads.

Admission: Free

Suffield on the Green & Craft Fair — Suffield, CT

September 12–13, 2026

Suffield’s largest community event takes over the town green for its 55th year.

This isn’t an agricultural fair in the traditional sense. Instead, you’ll find local organizations, crafters, food, live music, children’s entertainment, bounce houses, alpacas, a free train ride, and other activities spread across the green.

It’s also one of those events that really gives you a feel for the community itself, which is one of my favorite things about local festivals.

Saturday: 10 a.m.–5 p.m.
Sunday: 11 a.m.–4 p.m.

Four Town Fair — Somers, CT

September 17–20, 2026

Now we’re talking history.

The Four Town Fair represents Ellington, Enfield, Somers and East Windsor and has held onto its agricultural roots while becoming one of Northern Connecticut’s signature September fairs.

Expect livestock and agricultural exhibits, rides, entertainment, contests and the kind of things you’d expect from a genuine New England country fair.

For anyone in the Enfield/Suffield area, this one absolutely belongs on the calendar.

Where: 56 Egypt Road, Somers

The Big E — West Springfield, MA

September 18–October 4, 2026

And then there’s the big one.

You can’t write a Western Massachusetts fair guide without The Big E.

For 17 days, the Eastern States Exposition essentially becomes its own city. There are agricultural competitions, rides, concerts, shopping, the Avenue of States and more food than any reasonable person should attempt to consume in one day.

But we’re New Englanders. Reason has very little to do with Big E food.

The fair draws visitors from all six New England states and well beyond, but when you live here, The Big E is simply part of September.

If you’ve never gone, go at least once. If you’ve lived here forever, you probably already have your own Big E traditions.

Where: Eastern States Exposition, 1305 Memorial Avenue, West Springfield

Simsbury Arts & Crafts Festival — Simsbury, CT

September 19–20, 2026 | 10 a.m.–4 p.m.

While The Big E is in full swing, Simsbury offers something considerably smaller and quieter.

The annual Arts & Crafts Festival features original work from artists and craftspeople, with proceeds from exhibitor fees supporting scholarships and charities throughout the Farmington Valley.

It’s a nice alternative if crowds, livestock barns and deep-fried everything aren’t your idea of a relaxing weekend.

Where: Simsbury Performing Arts Center, 22 Iron Horse Boulevard, Simsbury

Belchertown Fair — Belchertown, MA

September 25–27, 2026

Fair season isn’t over just because The Big E has started.

The Belchertown Fair runs during the final weekend of September and offers another opportunity to experience a smaller community fair while everyone else is fighting traffic on Memorial Avenue.

It’s another long-running local tradition built around agriculture, community and family activities.

ARToberFEST — Westfield, MA

Saturday, September 26, 2026 | 10 a.m.–4 p.m.

If your preferred fall festival involves more art than livestock, come back to downtown Westfield for ARToberFEST.

The annual outdoor fine arts festival takes place throughout the Downtown Westfield Cultural District and brings together fine artists, artisans, and authors. Organizers have room for more than 80 exhibitors, and all of the work is original and juried.

Painting, photography, sculpture, printmaking, glass, wood, clay, metalwork and original literature are all part of the mix.

I like this one because it’s a completely different way to spend a fall Saturday — wandering downtown, looking at art and seeing a different side of Westfield.

Where: Downtown Westfield Cultural District
Rain date: Saturday, October 3

Riverton Fair — Riverton, CT

October 9–11, 2026

By October, we’re firmly into actual fall.

The Riverton Fair takes place in historic Riverton, in the northwest corner of Connecticut, and is put on by the Union Agricultural Society of Barkhamsted, Colebrook and Hartland.

There are rides, animals, food, music and agricultural competitions, along with some wonderfully old-fashioned fair contests including woodchopping, axe throwing, skillet throwing and hay-bale tossing.

This is also a gorgeous time of year to make the drive into northwest Connecticut.

Go for the fair. Enjoy the foliage. Eat something you probably shouldn’t.

PumpkinFest — Westfield, MA

Saturday, October 17, 2026 | 11 a.m.–3 p.m.

And we’re bringing the guide back home to Westfield to finish.

Westfield on Weekends’ eighth annual PumpkinFest takes place on the athletic fields behind Amelia Park and the Boys & Girls Club.

If you’ve never been, this isn’t a quiet little pumpkin display. PumpkinFest has grown into one of Westfield’s big fall community traditions, drawing families for an afternoon centered around pumpkins, entertainment, and seasonal fun.

The complete 2026 program is still being developed, so I’ll update this guide as more details are announced.

What we do know is that PumpkinFest is happening rain or shine, which means New England October weather doesn’t get a vote.

When: Saturday, October 17, 11 a.m.–3 p.m.
Where: Athletic fields behind Amelia Park/Boys & Girls Club, off South Broad Street, Westfield
Rain or shine

And with that, I think we can officially call fair season over.

Probably.

Save This Guide — I’ll Keep Updating It

One of the things I love about living here is that you don’t have to travel very far to find something happening.

I’ve lived in Western Massachusetts my whole life, and I’m still discovering events, farms, traditions, and places I didn’t know about. That’s part of why I put these local guides together.

I’ll update this guide as schedules change or I find something I’ve missed. If there’s a Western Massachusetts or Northern Connecticut fair, farm day, or fall festival that absolutely belongs here, let me know.

And if you’re new to the area — welcome. Go explore.

Event information is current as of August 2026. Dates, admission prices, locations, and schedules can change, so always check with the event organizer before heading out.

Looking for More Things to Do?

Fair season may be one of my favorite stretches of the local calendar, but it definitely isn’t the only time there’s something happening around here.

If you’re planning ahead — or you’re one of those people who wants to know where everybody is going before you see the pictures on Facebook the next morning — I have a couple of other local guides that can help.

Fireworks in Western Massachusetts & Northern Connecticut

Summer around here comes with plenty of opportunities to throw a blanket in the car, find a patch of grass and wait for the sky to light up.

My Western Massachusetts & Northern Connecticut Fireworks Guide rounds up local displays, dates, locations, and event details so you don’t have to hunt through twenty different town Facebook pages trying to figure out where the fireworks are this weekend.

→ [See the 2026 Fireworks Guide]

Free Summer Concerts in Western Massachusetts & Northern Connecticut

One of the best things about summer in New England is how many towns put on free outdoor concerts.

From town greens and parks to community pavilions, my Free Summer Concert Guide collects the local concert series happening throughout Western Massachusetts and Northern Connecticut in one place.

Bring a chair, pack something to eat and enjoy the fact that sometimes a really good night out doesn’t have to cost anything.

→ [See the 2026 Free Summer Concert Guide]

Vineyards & Wineries in Western Massachusetts & Northern Connecticut

You don’t have to travel to Napa — or even leave New England — to spend an afternoon at a vineyard.

My Local Vineyards & Wineries Guide takes you around Western Massachusetts and Northern Connecticut, with places to taste local wines, sit outside with friends, catch some live music, and enjoy some really beautiful New England scenery along the way.

→ [Explore the Local Vineyards & Wineries Guide]

Breweries in Western Massachusetts & Northern Connecticut

If beer is more your speed, we’ve got plenty of that too.

The local craft beer scene has grown enormously over the years, from small neighborhood taprooms to destination breweries worth building an afternoon around. My Local Brewery Guide will help you find some of the breweries worth exploring throughout Western Massachusetts and Northern Connecticut.

→ [Explore the Local Brewery Guide]

Between the fairs, festivals, fireworks, concerts, vineyards, and breweries, there really is a lot happening in our little corner of New England.

You just have to know where to look.