By Robyn Wolcott

The fall air has started to infiltrate our long summer days, and as traditional New Englanders, it’s hard not to be at least a little happy about what’s to come from pumpkin flavored everything to the gorgeous foliage. I always say that the best part of living here is that you get to experience all of the seasons – and hopefully, like me, you enjoy something about each.

Fall Fairs, Antiques & Eats

Madison is a perfect spot to spend a weekend or overnight as you aim to enjoy some fall staples in the area. With the Guilford Fair just next door to Madison running September 15-17, enjoy fair food, music, entertainment, animals, tractors, a parade, and more after a great breakfast in Madison. Then come back to town for a little shopping or leisure before snuggling into bed with the windows open to let in that fall air.

If you’re into antiques, vintage items, or re-purposed goods, the Madison Chamber hosts a fantastic shopping event on the Madison Green that same weekend on Saturday, September 16. Interested? Take a screenshot or print out this coupon for a discount to attend!

The following weekend, you can take Route 79 straight up to Durham Fair for an event that has been in existence for 100 years. Running from September 21-24, this fair has huge exhibits, rides, games, livestock, giant pumpkins and other plants to see, crafts, baking, art, a wine festival, all types of kids activities and exhibits, and a farm museum to catch the history.  Sunday the 24th is also Military Appreciation Day during which all US Active Military and US Veterans receive free admission.

You should start your weekend early because each Friday, you can get a taste of fall by visiting the Farmers’ Markets on the Madison Green. This runs every Friday through October.

Car Shows

If you’re a big car fanatic, there are two fun events coming up this month: British Wheels on the Green on Saturday, Sept 23 starting at 10am.

Hearth at Tuxis Pond’s Classic Car Show on Saturday, Sept 30 starting at 10am. Cars, music, food, and ice cream! Proceeds will be donated to disabled American veterans.

The Scarecrows are Coming

As we head into October, start watching for the scarecrows as they invade Madison! It’s all in good fun as part of the Madison Chamber’s Scarecrow Contest.  Click here for details to get involved if you’re a business in town!

If you need help planning your time in Madison, contact the Madison Chamber at or 203.245.7394. Happy Fall!