Fall fun is on its way to Fairfield County! Here’s a few exciting upcoming events you can look forward to in the coming cool weather months.
Events in Fairfield
Oktoberfest, September 14, 2024, from 2-6 pm
70 Sanford St, Fairfield, CT, 06824
Fairfield is hosting its second annual Oktoberfest on Saturday, September 14th, from 2 to 6 p.m. The Parks and Recreation Department, Experience Fairfield, and Fairfield Theater Company will co-host the event. The festival will feature a selection of seasonal beers, local food trucks, live music, and more.
Food Truck Festival - September 22, 2024 at 11 am
Jennings Beach, 880 S Benson Rd, Fairfield, CT, 06824
If you’re looking for a fun way to spend your Sunday, look no further. Stop by the annual Fairfield Food Truck Festival at Jennings Beach on Sunday, September 22. There will be a wide variety of food trucks and menu selections. All proceeds from the event will benefit the Fairfield Public Library.
Bags n’ Brews - October 26, 2024 12pm
111 Black Rock Tpke, Fairfield, CT, 06824
The Fairfield Fire Fighters Charitable Foundation is going to be hosting a cornhole tournament at Elicit Brewing Company. The benefits from this event will go to members of the department's families who are directly dealing with cancer. The event will offer food, beer, and raffles. Admission for spectators is free, and it costs $100 per team to enter the tournament.
Events in Westport
Westport is your Oyster - September 27, 2024 from 5-7pm
25 Avery Pl, Westport, CT, 06880
The Westport Museum will host an evening of events in the museum gardens. People can enjoy live music, lawn games, cocktails, shellfish shuckers, and admission to a museum exhibit. Tickets will be $65 per person, and you can purchase them ahead of time online or get one in person. However, tickets will be in limited supply at the door. Your ticket includes a dozen oysters, prosecco, refreshments, and museum admission.
Fall Festival - October 6, 2024, at 10 am
Earthplace, 10 Woodside Ln, Westport, CT, 06880
Come to this fall festival with friends and family on Sunday, October 6th. You will enjoy food trucks, a climbing wall, a corn pool, an apple slingshot, a donut on a string, animal encounters, nature, and so much more. Tickets for adults are $10, for children two and up, they are $5, and anyone younger is free.
Monte Carlo Masquerade - October 26, 2024 at 7 pm
Westport Woman’s Club, 44 Imperial Ave, Westport, CT, 06880
The Westport Museum is hosting a night of fun for its Monte Carlo Masquerade. At this event, you can play casino games, enjoy cocktails, great food, and more! Pre-sale tickets will be available through September 26th for $125, and tickets bought at the door will cost $150. All proceeds from the event will go towards the museum’s exhibitions, programs, and research.
Events in Danbury
Moose Lobsterfest - September 21, 2024 at 12 pm
75 Boulevard Dr, Danbury, CT, 06810
The Danbury Moose Lodge is putting on its second annual lobster fest on Saturday, September 21st. Tickets are $40 online until Saturday the 14th, and you can also get tickets at the door on the day of the event for $50. Tickets ordered beforehand will guarantee a choice of steak or lobster and a drink and sides. There will also be more food available at the event. One DJ and two bands will play live music throughout the day.
The Greater Danbury Irish Festival - September 21-22, 2024 12pm
1 Ives St, Danbury, CT, 06810
The Greater Danbury Irish Festival is a free two-day event that you will not want to miss. Over the two days, they will have all sorts of entertainment that represents Irish culture. Come out to dance along to Irish music and see Irish step dancers. They will have food available to purchase, a raffle, and games for kids.
Events in Milford
Crumbl Cookie Ribbon Cutting - September 20, 2024 at 3 pm
1642b Boston Post Rd, Milford, CT, 06460
Come to the grand opening of the new Crumbl Cookie in Milford. This event is completely free and open to the public. Here, you can purchase a wide selection of new and delicious cookies. With new flavors that change each week, this will be an event you do not want to miss.
Trunk or Treat - October 31, 2024 at 5:30 pm
Wildermere Beach Congregational Church, 133 Broadway, Milford, CT, 06460
Stop by the Church on Halloween and enjoy a trunk-or-treat. This event is free for all adults and kids who attend. You can enjoy candy, cider, apples, donuts, and more. Swing by the church before going out trick-or-treating and enjoy the free treats they will offer.
Events in Orange
Yoga at Stappa Vineyard - September 29, 2024 at 10 am
Stappa Vineyard, 403 Derby Ave, Orange, CT, 06477
Have a fun Sunday morning by doing yoga at the beautiful Stappa Vineyard in Orange, CT. For $27, you can enjoy this yoga class and get a complimentary snack bag. After the class, feel free to stay and look around, explore the vineyard, and purchase wine.
Events in Derby
Paranormal Dinner and Ghost Tour - October 3, 2024 at 6 pm
Twisted Vine Restaurant, 285 Main St, Derby, CT, 06418
If you enjoy ghosts and all things supernatural, then this is the event for you. There will be a buffet dinner with all sorts of delicious food that you will not want to miss out on. At the event, there will also be a cash bar. After dinner, you will go on a ghost tour of the building and get to hear stories of paranormal activity. You might even get to see some paranormal activity.
