CBA Events

The Charlestown Business Alliance (CBA) is proud to host a variety of events that bring together the community, promote local businesses, and foster connections. Whether you’re enjoying the spring festivities or celebrating the holiday season, our events are designed to make Charlestown a vibrant and thriving place to live, work, and shop.

Street view with a sidewalk, parked white Jeep, traffic, and a flag with red and blue colors hanging outside a building, seen through a glass window.
Front of a boutique shop named Monroe with black awnings and door, bicycle with a basket parked outside, potted plants with white flowers, and a sign indicating it is open.

May Day

Every first Saturday in May, the CBA hosts May Day, a lively spring event that showcases the best of Charlestown’s local businesses. This community celebration is a chance to enjoy the season’s fresh energy, discover unique products and services, and connect with your neighbors.

Local businesses - ranging from restaurants to retail stores - open their doors for a day of special offers, promotions, and entertainment. May Day is the perfect way to celebrate the arrival of spring while supporting Charlestown’s entrepreneurs and creatives. It's an event for the whole family, offering something for everyone to enjoy.

Learn More About May Day Here!
A street sign reading 'MONUMENT SQ' attached to a black lamppost with a lit vintage-style street lamp on top, against a background of trees and park scenery.
An outdoor dining scene at dusk with string lights, trees, pink flowers, and people sitting at tables in front of a brick building on a city sidewalk.

Holiday Night Out

In December, the CBA hosts our annual Holiday Night Out, a festive celebration designed to get the community in the holiday spirit. This event allows Charlestown residents and visitors to shop local, dine in the neighborhood, and enjoy the festive atmosphere created by our local businesses.

Holiday Night Out features special promotions, sales, and holiday-themed activities throughout the evening. It’s a chance to cross off your holiday shopping list, enjoy delicious food and drinks, and participate in a community celebration of the season. Whether you’re looking for gifts or just want to enjoy a night out, Holiday Night Out is a great way to support Charlestown’s small businesses while having fun with friends and family.

Learn More About The Holiday Night Out Here!
Outdoor dining area with string lights, featuring a stone wall, a wooden door with a sign that reads Dovetail, and blurred people sitting and walking around.
People dining outdoors at a restaurant with red umbrellas and a large tree in front, in an urban setting with a building in the background.

CBA Networking Events

In addition to our large annual events, the CBA hosts Networking Happy Hours throughout the year. These events offer business owners the chance to connect, share ideas, and collaborate with one another. These informal and relaxed gatherings provide a valuable opportunity for Charlestown businesses to grow their networks, exchange tips, and foster partnerships that benefit the community.

As part of your membership, you’ll have access to three Networking Happy Hours each year—designed to help you make meaningful connections and strengthen the local business ecosystem.

Learn More About Upcoming Networking Events Here!
Outdoor patio of a restaurant with people dining, string lights, trees, and a building with a sign that says 'Daretail' on a beige wall.
Sunlit view of a steep residential street in San Francisco with Victorian-style houses, cars parked along the curb, and city skyline in the background.

Homecoming Weekend

In early fall, the Charlestown Business Alliance hosts Homecoming Weekend, a neighborhood-wide celebration that marks the return from summer and the start of a new season in Charlestown. The event invites residents and visitors to come together, reconnect, and enjoy everything our local businesses have to offer after the slower summer months.

Homecoming Weekend features restaurant specials, pop-up events, and exclusive deals at local shops, along with fun community activities that highlight Charlestown’s small business spirit. Whether you’re dining out, shopping local, or just catching up with neighbors, it’s the perfect way to welcome fall and support the businesses that make Charlestown such a vibrant place to live and work.

Learn More About The Homecoming Weekend here!