Things to Do in Frederick MD This Weekend: 5 Worth Leaving the House For

Last updated on September 14th, 2026

This week’s picks: September 17–20, 2026

Looking for things to do in Frederick, MD this weekend without scrolling through a giant event calendar? I’m a longtime Frederick County local, and every week I narrow down what’s happening to five events I think are actually worth leaving the house for.

This isn’t a list of everything happening in Frederick. It’s my short list of what stood out for September 17–20, 2026, so you can spend less time searching and more time actually doing something fun.

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Why These 5 Made My List

There are always plenty of Frederick events to choose from. I look for the ones that feel special, have strong local interest, and give you a good reason to get out of the house. I also try to mix it up so you’re not getting five versions of the same thing.

Here’s what’s worth getting out of the house for this weekend…

Pam’s Top 5 Things to Do in Frederick This Weekend

1. 💃 Alive @ Five: Costas Colectivo

Costas Colectivo performing salsa music at Alive @ Five in Downtown Frederick, Maryland.
Photo credit: Costas Colectivo

📅 When: Thursday, September 17, 2026, 5–8pm
📍 Where: Carroll Creek Amphitheater, Downtown Frederick
💲 Cost: Check event page for admission details
🎶 Best for: Live music, dancing, happy hour, and kicking off the weekend early

Ready to add a little salsa to your Thursday night? Costas Colectivo takes the Alive @ Five stage this week with a lively Latin sound that might make standing still a challenge. Grab a drink, meet up with friends, and soak up one of the last Thursday evenings of the Alive @ Five season.

🔗 More Info: Alive @ Five: Costas Colectivo

2. 🎡 The Great Frederick Fair

The Great Frederick Fair at the Frederick Fairgrounds in Frederick, Maryland.
Photo credit: The Great Frederick Fair

📅 When: Friday, September 18–Saturday, September 26, 2026; Friday 4–10pm, Saturday onward 9am–10pm
📍 Where: Frederick Fairgrounds, Frederick, MD
💲 Cost: $10 online/$15 at the gate for ages 11+; kids 10 & under free
🎠 Best for: Fair food, rides, live entertainment, agriculture, and a Frederick tradition

You know September has officially arrived in Frederick when the fairgrounds light up! The Great Frederick Fair kicks off Friday for nine days of fair food, carnival rides, animals, exhibits, live entertainment, and all the people-watching you could possibly want. Come hungry because we all know the food is half the reason we go.

🔗 More Info: The Great Frederick Fair

3. 🎃 Ladies Night @ Jumbo’s

Ladies Night at Jumbo’s Pumpkin Patch in Middletown, Maryland.
Photo credit: Jumbo’s Pumpkin Patch

📅 When: Friday, September 18, 2026, 6–9pm
📍 Where: Jumbo’s Pumpkin Patch, Middletown, MD
💲 Cost: Check event page for admission details
👯‍♀️ Best for: Friends, fall fun, shopping, and a Friday night out

Grab your girlfriends because Jumbo’s is giving us a pretty good excuse for a fall night out! Head to the pumpkin patch for Ladies Night and enjoy an evening at one of Frederick County’s favorite fall destinations. Pumpkins, friends and a September evening in Middletown? Yep, that’ll do.

🔗 More Info: Ladies Night @ Jumbo’s

4.🍺 Kilometers & Kegs

Kilometers & Kegs 5K and Fun Run at the Thurmont Carnival Grounds in Thurmont, Maryland.
Graphic credit: Cool’s Legacy Inc.

📅 When: Saturday, September 19, 2026, 10am–2pm
📍 Where: Thurmont Carnival Grounds, Thurmont, MD
💲 Cost: Registration required for the 5K/Fun Run
🏃‍♀️ Best for: Runners, walkers, beer lovers, and supporting a good cause

Run it, walk it, then celebrate with a cold one! Kilometers & Kegs includes a 5K and Fun Run followed by food, beer and activities at the Thurmont Carnival Grounds. Even better, proceeds support organizations working in suicide awareness, prevention and support, so those kilometers are going toward something that matters.

🔗 More Info: Kilometers & Kegs

5.🍻 Oktoberfest at the Farm

Oktoberfest at the Farm at Prospect Point Brewing in Frederick, Maryland.
Photo credit: Prospect Point Brewing

📅 When: Saturday, September 19, 2026, 11am–10pm
📍 Where: Prospect Point Brewing, Frederick, MD
💲 Cost: Check event page for details
🥨 Best for: Craft beer, fall vibes, friends, and Oktoberfest fun

Break out the pretzel appetite because Oktoberfest season is here! Prospect Point Brewing is celebrating at the farm with a full Saturday of Oktoberfest fun. It’s an easy way to spend a September afternoon or evening outside with friends, a beer in hand, and just enough German-inspired fun to make you wonder whether you actually need lederhosen.

🔗 More Info: Oktoberfest at the Farm

⭐ If I Were Picking Just One…

My pick this weekend: The Great Frederick Fair. My husband and I will be going, and I’m not even going to pretend it’s for the rides or the exhibits. 😂 We’re going for the FOOD. Give me all the once-a-year fair food, and I’ll happily call that our Friday night plans. 🎡🍟🍦

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Prefer video? I share these picks every Thursday on Facebook and Instagram, complete with photos and a quick overview of each event.

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FAQs About Things to Do in Frederick This Weekend

Where can I find Frederick County events every weekend?

I update this page every week with five Frederick-area events that stand out to me. Rather than listing everything on the calendar, I narrow it down to the events I think are most worth your time.

When is this Frederick weekend events guide updated?

I update my Top 5 each week with picks for the upcoming Thursday through Sunday, so check back before the weekend for the newest list.

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