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  4. Amazing May 2021 Events in New Haven
    That You Won’t Want to Miss!

Amazing May 2021 Events in New Haven
That You Won’t Want to Miss!


As we move further into Spring and towards Summer, New Haven becomes a cultural hub of activity. May is a month filled with annual art and music events that’ll get you inspired and enrich your perspectives. Although there are still pandemic restrictions and some of the traditional events won’t be back until 2022, there are some great outdoor and virtual options for you to explore.

Take a look at some of the best events of the season that take place throughout May. If you’re looking for something a little different from dining out (which will always be a favorite pastime in New Haven), why not add one or more of these events into the mix?


Westville Music Bowl

Opening at the end of April this year due to its covid related delay, Westville Music Bowl is hosting its first ever socially distanced concerts. Located opposite Yale Bowl, the former Connecticut Tenner Center will host outdoor concerts rain or shine!

The first acts to be performing are Gov’t Mule, Umphrey’s McGee, and Twiddle and there are plenty of others already booked in up to the end of June. If you find an act you want to see but it’s sold out, don’t fear just yet! Keep checking back at their website as performers are already adding more dates.

Seats are currently being sold in set of two or four with a minimum of 6 feet social distance from other seats. Get a group of friends together, go out for an early dinner downtown (check out Geronimo’s or Bar on Crown Street) and get the Yale Bus or drive up to Westville Music Bowl on Yale Ave.

westville music bowl

International Festival of Art & Ideas

Due to the pandemic, the IFAI reinvented their summer festival last year by launching an incredible 2-month virtual festival with over 200+ events and over 120,000 worldwide in attendance.

This year, there will continue to be mainly virtual events between May 14th and June 27th with 80% of them being free of charge! You’ll have the opportunities to witness the incredible works of choreographer Ronald K. Brown, Indigenous playwright and Forbes “30 under 30” theatre director Madeline Sayet as well as the fabulous Hair Art show.

As one of New Haven’s biggest cultural events in their annual calendar, this year’s theme is Imagine and the IFAI shares the full programming lineup and reservation spots in the Spring! So, go check it out now and see what amazing art you’ll find. If you’re watching a virtual show, why not invite some friends over and make a true event of it. Order in some insomnia cookies or grab a take out from Tikkaway on Orange Street.

ifai new haven

Westville Village ArtWalk

This community-based event is a free, annual art festival which spans three blocks in Historic Westville Village and Edgewood Park every Mother’s Day weekend (May 4th-8th). It’s a family friendly celebration filled with live music, art exhibitions and demonstrations, interactive art making, theatre performances, walk tours and so much more.

Traditionally this event draws in around 8,000 visitors. My favorite part of this event is the Artist, Artisan and Crafters Market which has over 30 vendors selling the most unique and stunning pieces.

As part of ArtWalk 2021, the second annual 6 Square Exhibition is taking place with all ages and abilities welcome to participate. Create your own artwork on a 6 by 6-inch square and submit it by the end of April to be involved.

It’s an event you won’t want to miss! You can either drive up Whalley Ave to get to Westville or take a short ride on the 241 or 243 bus from New Haven Green. When you’re roaming around the exhibitions and market stalls, why not grab a refreshing drink from Pistachio on the corner of Whalley Ave and Blake Street! Their fruit smoothies are the best around.

Westville Village ArtWalk

Drive-In Live Concerts

For something a little different, you can head out to Connecticut Post Mall in Milford and enjoy their drive-in concerts this spring. The Milford Performance Center has decided to do this concert series in 2021 as an outdoor alternative to their usual auditorium concerts.

Get tickets to see these bands and more:

  • Queen Meets The Kings
  • Last Child – Best Bad Boys of Boston Aerosmith Experience
  • Creamery Station
  • No Quarter

If you don’t have a car, but do have a license, you can always hire one by the hour with Zipcar. As you drive down Boston Post Road to the event, you’ll find lots of restaurant/drive-thru options to take with you.

Have a wonderful May in New Haven! It’s a lovely time of year to get out and explore the city and its surroundings. We’re hoping the many more amazing events that New Haven hosts will return in Spring 2022 as well as Yale’s art museums, the in-person theatres and open studios.

Drive-In Live Concerts