Spring Into the Scene: Boston's Must-Do Weekend Events
Kick off the first weekend of May with a curated lineup of can’t-miss events happening across the Boston area—from floral strolls and rooftop sips to Derby flair and local maker markets. Whether you’re in the mood for a cozy cheese and wine class, a golden-hour garden walk, or an all-out Cinco de Mayo bash, there's something for every vibe and every kind of weekend warrior. We’ve rounded up five standout happenings to add to your calendar—so grab your friends, plan your fits, and get ready to soak up spring in the city. Here's where to go, what to do, and how to make the most of May. Let’s dive into the lineup!
Here are someAMAZINGthings to do this weekend!
Italian Wine and Cheese, The Perfect Pairing @ CCAE: Friday, May 02, 2025 6:00p - 8:00p
If you're looking for a cozy and inviting way to spend your Friday night, Bonde Social Club is the place to be. This charming wine shop transforms into a lively social spot, offering an expertly crafted antipasto board of the day ($18 per person) and a rotating selection of wines listed on their blackboard. Guests can enjoy the warm ambiance while listening to vinyl records—either from the shop’s collection or their own (BYOV!). It's a perfect blend of great food, fine wine, and community spirit in a relaxed setting.
Italian Wine and Cheese, The Perfect Pairing @ CCAE: Friday, May 02, 2025 6:00p - 8:00p
If you're looking for a cozy and inviting way to spend your Friday night, Bonde Social Club is the place to be. This charming wine shop transforms into a lively social spot, offering an expertly crafted antipasto board of the day ($18 per person) and a rotating selection of wines listed on their blackboard. Guests can enjoy the warm ambiance while listening to vinyl records—either from the shop’s collection or their own (BYOV!). It's a perfect blend of great food, fine wine, and community spirit in a relaxed setting.
Spring BloomFest: Sunset After Hours: Friday, May 02, 2025 5:00p - 7:00p
Celebrate the beauty of spring at Spring BloomFest: After Hours at the stunning Stevens-Coolidge House & Gardens in North Andover, MA. Stroll through seven breathtaking gardens filled with tulips, daffodils, and vibrant spring blooms, all bathed in golden sunset light. Guests will enjoy live music, a complimentary drink from Marble Ridge Winery, and a charcuterie cup from June & Honey—perfect for an evening picnic!
Spring BloomFest: Sunset After Hours: Friday, May 02, 2025 5:00p - 7:00p
Celebrate the beauty of spring at Spring BloomFest: After Hours at the stunning Stevens-Coolidge House & Gardens in North Andover, MA. Stroll through seven breathtaking gardens filled with tulips, daffodils, and vibrant spring blooms, all bathed in golden sunset light. Guests will enjoy live music, a complimentary drink from Marble Ridge Winery, and a charcuterie cup from June & Honey—perfect for an evening picnic!
Derby on the Rooftop Rooftop at Revere: Saturday, May 03, 2025 4:00p - 8:00p
Saddle up for Derby Day at Lantern Lounge, where Southern charm meets city skyline at Boston’s largest rooftop! Celebrate in style with two classic Woodford Reserve Mint Juleps and a delicious spread of small bites from the brand-new summer menu. Enjoy live coverage of the Kentucky Derby on the big screen as you mix, mingle, and soak in the festive atmosphere. Don your most fabulous hat or dapper fedora for a chance to win an overnight stay at the Revere Hotel in the show-stopping Hat Contest. It’s the ultimate rooftop celebration—elegant, elevated, and full of Derby Day flair!
Derby on the Rooftop Rooftop at Revere: Saturday, May 03, 2025 4:00p - 8:00p
Saddle up for Derby Day at Lantern Lounge, where Southern charm meets city skyline at Boston’s largest rooftop! Celebrate in style with two classic Woodford Reserve Mint Juleps and a delicious spread of small bites from the brand-new summer menu. Enjoy live coverage of the Kentucky Derby on the big screen as you mix, mingle, and soak in the festive atmosphere. Don your most fabulous hat or dapper fedora for a chance to win an overnight stay at the Revere Hotel in the show-stopping Hat Contest. It’s the ultimate rooftop celebration—elegant, elevated, and full of Derby Day flair!
Cinco De Drinko with DJ Costa @ Big Night Live ( 21+ ): 10 PM
Get ready to fiesta at Cinco de Drinko with Costa at Big Night Live—Boston’s hottest spot for an unforgettable night out! This 21+ celebration is bringing all the energy with Latin beats, bold drinks, and a crowd ready to party. Sip on handcrafted cocktails, dance the night away, and soak up the electric vibes all night long. Hosted by Costa, this event promises surprise guests, top-tier entertainment, and non-stop fun. Don’t miss your chance to celebrate Cinco in style—grab your tickets and let’s get this party started!
Cinco De Drinko with DJ Costa @ Big Night Live ( 21+ ): 10 PM
Get ready to fiesta at Cinco de Drinko with Costa at Big Night Live—Boston’s hottest spot for an unforgettable night out! This 21+ celebration is bringing all the energy with Latin beats, bold drinks, and a crowd ready to party. Sip on handcrafted cocktails, dance the night away, and soak up the electric vibes all night long. Hosted by Costa, this event promises surprise guests, top-tier entertainment, and non-stop fun. Don’t miss your chance to celebrate Cinco in style—grab your tickets and let’s get this party started!
Sip & Shop in Boston - Makers Market by Pop Up Gallery: Sunday, May 04, 2025 12:00p - 4:00p
Mark your calendars for a fun-filled afternoon at the Sip & Shop event, happening Sunday at The Great American Beer Hall in Medford! This lively, family-friendly market brings together local makers, crafters, and artists for a day of sipping, shopping, and supporting small businesses. Discover everything from houseplants and handmade candles to jewelry, macramé, and more—perfect for gifting or treating yourself. With free admission, pet-friendly vibes, and plenty of good drinks to enjoy, it’s the perfect way to spend a sunny weekend afternoon. Don’t forget to follow along on Instagram for updates and vendor spotlights!
Sip & Shop in Boston - Makers Market by Pop Up Gallery: Sunday, May 04, 2025 12:00p - 4:00p
Mark your calendars for a fun-filled afternoon at the Sip & Shop event, happening Sunday at The Great American Beer Hall in Medford! This lively, family-friendly market brings together local makers, crafters, and artists for a day of sipping, shopping, and supporting small businesses. Discover everything from houseplants and handmade candles to jewelry, macramé, and more—perfect for gifting or treating yourself. With free admission, pet-friendly vibes, and plenty of good drinks to enjoy, it’s the perfect way to spend a sunny weekend afternoon. Don’t forget to follow along on Instagram for updates and vendor spotlights!
No matter how you choose to spend it, this weekend is packed with vibrant experiences that celebrate the best of spring in and around Boston. From sipping mint juleps on a rooftop to browsing handmade treasures at a local market, there's something for everyone to enjoy. So mark your calendars, grab your tickets, and get ready to make some unforgettable memories. Don’t forget to support local businesses, snap some photos, and most importantly—have fun! Here’s to a weekend full of sunshine, good vibes, and new adventures.
