🌴 The Best Fall Things To Do This Weekend & Charleston's Best Italian

Hello Palmetto Parents!

We hope you enjoyed your first full week of fall! 🍂 I kicked mine off with a little adventure. My daughter and I joined a few other moms for a weekend in Black Mountain, North Carolina. We had so much fun: matching pajamas, our own cozy fire (that we made ourselves), and staying up way too late chatting. It was the kind of weekend that fills you up in the best way. If you want to see more, check out our Instagram for highlights and a few recommendations from the trip!

This week’s newsletter is packed with family fun: free admission to Boone Hall Farms, a family festival that takes you back to 1820, fall markets and festivals on John’s Island and Mount Pleasant, and our pick for the best Italian in Charleston (spoiler: it’s not Indaco). We’ve also included a little heart-to-heart about why sometimes the best choice is to ignore all the recommendations, stay home, and make your own fun.

If you’re looking for the ultimate fall weekend with your kids, the Boone Hall Pumpkin Patch is a must. Since 1997, this festival has grown into one of the largest in South Carolina, and 2025 marks its 29th year as a beloved Lowcountry tradition. We go every year, and it’s become one of our favorite family traditions. Our kids always have the best time running around and by the end of the day they’re completely filthy… which is really just proof they had a blast!

It does tend to get hot, so we always recommend waking up early and getting there right when the gates open. Hours are Fridays, Saturdays, and Sundays from 10am- 5pm and their season runs until October 26th. Tickets are $15 for ages 3 and up. Kids 2 and under are free (with an adult). Pro tip: head to the farm this Friday (October 3rd) admission is free!

Your admission gets you access to the Starling Chevrolet Corn Maze, a Family-Friendly Halloween Tractor Tour, Circus Incredible featuring the Flying Wallendas, Doc’s Variety & Magic Show, All-American Pig Races, Petting Zoo, inflatables, a honeybee exhibit, rubber duck races, agri-golf, and live performances on the Homegrown Stage. For an extra fee, your little ones can enjoy pony rides, face painting, and body art. And of course, don’t leave without picking out pumpkins by the pound and indulging in festival food favorites.

A quick note: pets must stay at home (service animals only) and there are port-a-potties on site.

Boone Hall’s Pumpkin Patch is the kind of event that brings families together, creates memories, and sets the tone for the entire fall season. 🎃🌽

For all the moms and dads of both two-legged and four-legged kids—this one’s for you! 🐾 Twice a month, we’ll fetch the latest on pup-friendly restaurants, tail-wagging events, and the best local spots to explore with your furry family member. Charleston is basically a dog’s paradise, and we’re here to make sure you and your pup never miss a treat.

If you’re looking for the perfect family outing this Saturday, mark your calendar for Family Day at the Aiken-Rhett House Museum on Saturday, October 4, from 3-6 pm. Now in its fourth year, this event has quickly become a Charleston favorite, and for good reason. The timing makes it ideal for families: a post-nap adventure for little ones that flows right into an early dinner.

You’ll be stepping back in time at the beautifully preserved c.1820 Aiken-Rhett House on Charleston’s historic peninsula, the afternoon offers a unique blend of history, fun, and community. Families can explore the home and grounds while enjoying activities designed for every age. Kids can embark on a scavenger hunt, try their hand at archaeology, or join in historic games. Crosswind Farms will bring a petting zoo, while Kristy Bishop Studios offers a live indigo dyeing demonstration. There will also be calligraphy lessons with Love Letter Gray Calligraphy and a sweetgrass basket weaving demonstration—hands-on experiences that bring Charleston’s heritage to life.

Food and music round out the day. Guests will enjoy a BBQ feast with sides provided by Charleston Outdoor Catering, all while listening to live music from The Only One JP Band. Adults 21+ will also receive two drink tickets for beer or wine with admission, making it a fun day for parents as well.

Tickets are $25 for adults (21+), $20 for PreserVISIONist Members, $18 for ages 4–20, and free for children 3 and under. All proceeds support the Historic Charleston Foundation, whose mission is to preserve the city’s rich history and advocate for a sustainable future—including work to protect Charleston’s homes, neighborhoods, and public spaces.

Whether your family loves history, animals, crafts, or just a good BBQ, this event has something for everyone. Don’t miss the chance to celebrate, learn, and play at one of Charleston’s most iconic historic homes.

After braving Costco on a Saturday morning (seriously, you deserve a medal), treat yourself and the family to a relaxing, free outing at Rooted Bottle Market & Wine Bar in Mount Pleasant. They’re hosting a family-friendly community market at 3510 Park Ave in Mount Pleasant from 10:30am-1:30pm this Saturday, and it’s the perfect way to kick off your weekend.

Families can enjoy live entertainment, shop from local vendors, and let the kids explore fun activities designed just for them. Whether it’s a chance to browse unique local goods, listen to music, or let the little ones burn off some energy, there’s something for everyone. You can find more details here.

It’s a relaxed, low-pressure way to spend a Saturday morning and a great stop after the chaos of running errands. Bring some chairs, bring the family, and soak up the fall vibes while supporting local businesses. All without spending a dime (unless you want to 😉)!

I normally avoid the road between Johns Island and West Ashley whenever I can. Little did I know, a perfect local brewing company sits right there, Edisto River Brewing. And this Saturday, that’s exactly where you want to be!

Join the Fall Festival Sip & Shop on Saturday, October 4, from 1-5pm for an afternoon full of community fun at Edisto River Brewing. This free event is packed with something for everyone: shop from 30 unique local vendors, visit the always-popular Crosswind Farms petting zoo, and grab a bite from Gaucho Grill Food Truck while you enjoy live music from Ron Daniel. Kids will love getting their faces painted by The Paint Pixie, while parents can sip on craft brews and browse the market.

It’s one of our favorite fall events of the season and not only because it’s free, but because it’s the perfect way to support local businesses while making family memories. Invite your friends for a Saturday that combines shopping, food, music, and community in one cozy local spot.

I grew up going to the North End in Boston. The Italian food heaven. Think two-hour lines for cannoli and grandmothers yelling in the kitchen. I know Italian food, and in Charleston I always tell people: skip Indaco and head to The Obstinate Daughter on Sullivan’s Island.

It’s the spot we take visitors to impress them. Inside feels cozy and elegant, while the patio is coastal casual and kid-friendly. When we bring our kids, we go early and sit outside, it’s relaxed and perfect for families! The pizzas are outstanding, the Ricotta Gnocchi is a must, and dessert should be the chocolate mousse—or head downstairs to Beardcat’s Sweet Shop for house-made gelato and take-home treats.

There’s no kid’s menu, but pizza and a la carte options work perfectly. After dinner, stroll the beach or let little ones play at PARD Park across the street. It’s our kids’ favorite park in the Charleston area.

Hours: Lunch daily 11am–3pm, dinner 4pm–10pm (open until 11pm Fri–Sat), brunch Sat–Sun 10am–3pm. Pizza all day.
Cost: Small plates $8–20, pizzas $17–20, pastas $25–35.

Make sure to get reservations a few weeks in advance because this place isn’t a best kept secret anymore! Perfect for date night or family night, The Obstinate Daughter blends island charm with serious Italian flavor.

I love being on the go and checking things off my list, but I’ve realized my kids don’t always need a packed schedule. They’re big extroverts and often ask for playdates or trampoline park trips, but when I set the expectation that we’re just hanging at home (even if we go with no TV), they seem more at peace. In fact, studies have found that kids benefit from unstructured time at home, it boosts creativity, lowers stress, and even strengthens family bonds.

I’ll be honest: sometimes I feel pressure to do all the big fall events. Drive an hour, pay for parking, wait in line, and still somehow make it home in time for my littlest one’s nap. It can feel like a lot. And while my kids love the big outings I plan, the truth is they also light up when they get to do their own project at home, whether that’s building a fort, creating a craft, or just running around our neighborhood. As you can see above, one of our baby’s favorite activities is to watch our washer and dryer spin!

So if you’re feeling the same pressure, take a deep breath. The ideas in this newsletter are here for inspiration, not obligation. Sometimes the sweetest moments happen when you slow down, stay home, and let the day unfold simply. Fall doesn’t have to be full of grand adventures for it to feel magical. Sometimes a quiet afternoon at home is all it takes!

Here’s to a fall filled with big adventures and those cozy, slow days at home.

Love, Jenna