Make the Most of September’s First Weekend: Events You Won’t Want to Miss

The first weekend of September has arrived, and with it comes that perfect early-fall energy. The air is still warm, the days are just long enough, and the calendar is brimming with things to do. Whether you’re wrangling kids, planning a date night, or just ready to meet new people, this weekend has something waiting for you.

Families: Big Adventures, Small Moments

If you’re near Washington, D.C., the National Book Festival is a must-see. It’s not just about browsing shelves—it’s about watching stories come alive. Imagine your kids’ eyes lighting up as they meet the authors behind their favorite bedtime tales, while you sneak into a panel on history or memoirs. With interactive science stations and more than ninety authors in attendance, it’s an all-day playground for curious minds.

Over in Chicago, family time looks a little different—but just as delicious. Taste of Chicago is back in Grant Park, and it’s a feast for all senses. You can sample an iconic Rainbow Cone, sway to JoJo’s Saturday night set, and cap it off with a fireworks-meets-drone show that turns the skyline into a stage. Admission is free, but fair warning: your kids will definitely talk you into going back for seconds.

If your crew loves a good fairground, there are plenty of options. The DC State Fair is quirky and urban, proving you don’t need cows to have carnival fun. Head a little further out to Prince George’s County in Maryland, and you’ll find a more traditional setup—rides, contests, and all the fried treats you can carry. Down south, Houston offers its own family-friendly mash-up: a graceful Japan Festival with tea ceremonies and martial arts demos in Hermann Park, alongside the wonderfully odd In a Pickle Festival, which features everything from pickle-themed games to eating contests.

Couples: Sparks in the Air

Romance doesn’t have to mean white tablecloths and string quartets—it can be as simple as sharing a funnel cake or dancing in the grass. Couples looking for something memorable have their pick this weekend.

Start with Taste of Chicago if you’re nearby. Nothing says togetherness like splitting small plates under festival lights, and when JoJo hits the stage Saturday, it’s easy to forget the rest of the world. The show ends with fireworks and drones—built-in date night magic.

If you’re closer to D.C., jazz is the theme of the weekend. The Silver Spring Jazz Festival and Rosslyn Jazz Fest both offer smooth tunes outdoors, perfect for an evening stroll. Picture holding hands, a picnic blanket between you, and the music weaving through the crowd.

And for couples who want something different, there’s even a CouplesFest Weekend Extravaganza—a playful mix of workshops, activities, and speakers. It’s part retreat, part date night on steroids, with a little bit of something for every kind of pair.

Singles: Out and About

Not partnered up? This weekend brings plenty of ways to mix, mingle, or simply enjoy your own company.

In North Carolina, a Durham singles mixer offers a relaxed, structured space for ages 30–49 to meet new people without the chaos of online swiping. Think casual conversations, light activities, and maybe a few new numbers in your phone by the end of the night.

If you’re more spiritually inclined, the Singles Fellowship and Grace Girl Tea in Maryland blends community and encouragement in a calming setting. It’s a refreshing way to meet people in a space that’s more about genuine conversation than icebreakers.

And then there’s always music. From the jazz stages in D.C. to the endless venues in Austin, live shows this weekend double as natural conversation starters. Festivals and concerts are perfect for striking up chats—you’re already surrounded by people who love the same music you do.

A Weekend Made for Everyone

What’s great about this particular weekend is how many choices feel open-ended. Families can bond over books, food, and culture. Couples can find both energy and intimacy in festivals and music. Singles can dive into new communities, or just use the weekend as an excuse to explore.

So wherever you land—on a picnic blanket in Chicago, in the middle of a book signing in D.C., or sipping tea at a singles fellowship in Maryland—know this: the weekend isn’t about filling time, it’s about creating a story you’ll still talk about on Monday.

Pack the sunscreen, grab a friend (or a date, or your kids), and get ready. September 6–7 has all the makings of a weekend you’ll wish could last just a little bit longer.