September Events Across New England That Are Worth Traveling For


September is a great time to be from New England, or visit if you don’t live here. The scorching temperatures finally start to give way to cooler days and the first hint of autumn color reveals itself. There’s also a lot of wonderful things happening. So, it can be overwhelming trying to decide which events you should go to. I’ve done the work for you and hand-selected the events happening all across the region that are not only worth attending, but worth traveling for. 

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Brimfield Flea Market
Brimfield, Massachusetts
September 3-8 

This is the last Brimfield Flea Market run of the year! If you’ve never been, be prepared to do a lot of walking because it is the largest event of its kind in the country with thousands of vendors. Hours vary depending on which field you’re shopping in, but overall the hours are 8-5. Entry to the show is free, but you will have to pay to park. You can bring your own food and water but I suggest hitting up some of the wide variety of food trucks and concession stands on site. There’s a little something for everyone. This event is held rain or shine, so check the weather before you go and dress appropriately and be sure to check yourself for ticks afterward.  

The Big E
West Springfield, Massachusetts 
September 13-29

The New England tradition returns on September 13! The Big E is the 6th largest fair in the nation. There’s something for everyone to do there: attend concerts, car shows, see the parades, go on carnival rides, shop, or learn about agriculture and animals. One of my favorites is to walk the Avenue of the States and explore vendors that exemplify the heritage, food, and traditions of each New England state. There is plenty of food to be enjoyed from a variety of vendors including traditional fair food and new twists on classic New England cuisine. Advance tickets are already on sale.

Newport Mansions Wine & Food Festival
Newport, Rhode Island
September 19-22

Join fellow wine and food lovers at this refined event and taste magnificent wines from around the world. Set against the backdrop of the opulent of the Newport Mansions there will be food from local, regional, and national chefs. Additionally, you can look forward to celebrity chef appearances and demonstrations from acclaimed chefs such as Justin Chapple, the Culinary Director of Food & Wine. You can also attend educational seminars with leading food and wine experts. Other events include elegant galas and jazz brunches. 

Greenwich Wine and Food Festival 
Greenwich, Connecticut
September 20-21

The Greenwich Wine and Food Festival is a two-day event showcasing the culinary landscape of the area and celebrating innovation in the food and beverage industries. This event is rain or shine and tickets include food, wine, and live music. There are also various vendors in the Marketplace, selling their products. This year’s guests include Martha Stewart, Margaret and Geoffrey Zakarian, and Valerie Bertinelli among others. Also this year, Little Big Town will be performing. You must be 21+ to attend, no children or infants will be let in. 

Acadia Night Sky Festival
Bar Harbor, Maine
September 25-29

Acadia National Park is home to some of the only dark skies left in New England. Over 80% of the population lives under skies that are so polluted with artificial light they can no longer see the Milky Way galaxy that we call home. This festival celebrates the magnificent naturally dark skies of Downeast Maine which have been carefully preserved through thoughtful lighting ordinances and dark sky friendly lighting. There are workshops, speakers, and hands-on experiences such as paddling through the bioluminescent organisms in Castine Harbor under a blanket of stars and learning how to photograph the Milky Way.

What events are you interested in attending this month? Let me know down in the comments!


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