Upcoming Events in Downtown Middletown – 2025

Get ready for another exciting year in Downtown Middletown! With events happening year-round, there’s something for everyone. Whether you're a local or visiting, mark your calendars for these can't-miss occasions!

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Note, all dates and times are subject to change (and some are very likely to change). So please check back often as we will add event specific pages to our website

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February – Love Middletown
Celebrate the season of love with Love Middletown! This event is a perfect way to spread joy while exploring local businesses. With plenty of opportunities to shop, dine, and take in the heartwarming atmosphere, it’s an ideal outing for couples and families alike. Stay tuned for more details on promotions and activities—this event is bound to fill you with the spirit of community. Check out more details here.

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March – Restaurant Week
Savor the flavors of Middletown during our annual Restaurant Week! Local eateries will be offering delicious, specially crafted menus for foodies to indulge in. Whether you're a fan of hearty comfort food or something a bit more adventurous, you’ll find plenty of options to satisfy your taste buds. It’s the perfect time to try a new spot or revisit a favorite!

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April – Spring Charcuterie Crawl
Join us on April 24th, from 5 to 7 PM, for the Spring Charcuterie Crawl! Local businesses will showcase their finest meats, cheeses, and snacks. It’s the ultimate tasting experience where you can enjoy a variety of flavors while strolling through the town. This event is perfect for food lovers and those who appreciate a good spread!

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April – Yard Sale
Declutter, shop, and find unique treasures at the Downtown Middletown Yard Sale on April 12th. For just $5, you can participate and have your yard sale featured on our Google map for easy navigation. It’s a fun way to support local vendors while uncovering great finds!

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May – Mother’s Day Themed Event
Celebrate Mother's Day in style with our special event in May. Local businesses will offer exclusive deals and promotions to honor the incredible women in our lives. Whether you’re looking for the perfect gift or simply enjoying a relaxing day out, this event provides a wonderful way to support small businesses and make your mom feel extra special.

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June – Flag Day Celebration
Join us on June 14th for a Flag Day celebration at The Everett. From 45 minutes to an hour of festivities, enjoy a stage presentation that highlights the history and significance of this day. It’s a family-friendly event that brings the community together to honor our national pride.

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July – Just Peachy Scavenger Hunt & Family Fun Fest
Bring the whole family on July 19th for a fun-filled afternoon of scavenger hunting and games at the Just Peachy Scavenger Hunt & Family Fun Fest! From 3 to 7 PM, you'll explore the town, solve puzzles, and enjoy local activities. There will be something for all ages to enjoy in this delightful summer event.

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August – Peach Festival
In August, come celebrate all things peach at our annual Peach Festival! With a variety of peach-themed treats and activities, this festival is a sweet treat for all. Be sure to grab your bags and indulge in the delicious offerings from local vendors.

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September – Ladybug Festival
The Ladybug Festival in September is a vibrant celebration that will take place on Scott Street between Green and Main. With fun activities, great food, and entertainment, it’s a fantastic way to enjoy the fall season. Plus, we’ll have exciting surprises for the whole family to enjoy!

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October – Charcuterie Fall Crawl
Mark your calendars for October 9th from 5 to 7 PM, and join us for the Charcuterie Fall Crawl! This event is the perfect blend of delicious tastings and autumn vibes. Take in the colorful fall atmosphere while enjoying local charcuterie creations—an event you won’t want to miss!

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November – Tree Lighting, Small Business Saturday, & Lamppost Decorating
The holiday season kicks off on November 28th at 6 PM with our magical Tree Lighting ceremony! Experience the sparkle of the season as we light up the tree in the heart of Downtown Middletown. Leading up to the event, enjoy Lamppost Decorating starting November 24th. Be sure to vote for your favorite lamppost design on our website as we get into the festive spirit. Plus, don’t forget to celebrate Small Business Saturday and support our local shops during this festive time.

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December – Holiday Parade
Wrap up the year in style with the 2025 Downtown Middletown Holiday Parade on December 6th! This beloved event is filled with colorful floats, festive performers, and a special visit from Santa Claus. It’s a holiday tradition that brings the entire community together to celebrate the season with joy and cheer.

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We’re excited to bring all of these fantastic events to Downtown Middletown in 2025. While dates and details are subject to change, these events promise to create memories that will last a lifetime. Be sure to check back for updates, and get ready to experience the magic of the season all year long!