Bluegrass, a small-town gastro tour, and 230 miles of Ozark Trail
Day Trips for Southeast Missourians
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This week’s issue is a winter weekend guide with good food, fun music, and a reminder that some pretty cool stuff is closer than you think.
Day Tripping
Fredericktown, MO
Love food, will day trip? Today's featured winter excursion is a self-guided gastro tour through a lovely little Madison County town. I want you to Anthony Bourdain your way through Fredericktown, MO. It's more than a gas station stop on your way to a river. Somehow, this small town has stacked up unique local eats. Small but mighty...hungry. Mighty hungry.
Important logistics notes: Do not fill up at the first stop. Pace yourselves. It's not a race. It's a meat marathon. And you'll have more options if you go on a Saturday. Many places are closed or close early on Sundays.
One possible restaurant hopping itinerary:
Start with coffee: The Station at Sawyer’s Landing. I’ve said this before and I’ll say it again: this place is like a cozy hipster café married a national park lodge and then built a treehouse for your kids. Get coffee, breakfast bagels, avocado toast, smoothies. There are plenty of light options to start the tour.
Lunch-ish, but don’t go too hard yet: The Depot Cafe. Housed in a historic train depot, this is a tiny scratch kitchen doing soups, sandwiches, wraps, salads, and desserts, all made in-house. It’s comfortable in that “you could sit here a while” way. Great food, great service, quaint, homey, and easy to love.
The Depot Cafe, Fredericktown, MO., January 2026
Throw in a shop. The Rusted Wren. A boutique that blends down-home Southern with a Western twist. A cute little palate cleanser between meats.
Now we're warming up. The Pig BBQ. A Fredericktown classic. A retro 1950s diner housing all-American greasy godliness. If you want something hearty, nostalgic, and satisfying. Ta-da. Perfection in pork form.
Another break between bites. Millstream Gardens Conservation Area. If you need to walk some room into your gut, I'm going to throw it back to last week's issue and recommend the Tiemann Shut-Ins Trail. It's paved, short, and takes you straight to the dramatic rushing whoosh of the shut-ins water. Appetite reset! (I'm sure it's buried in snow right now, but it's there.)
Dinner. I'm so proud of you for making it this far. I commend your enthusiasm and digestive abilities. You're tougher than me. I haven't made it this far and therefore, cannot give you a first-hand recommendation, grasshopper. But the next time I'm in town, these two are on my radar: Woodstack Smokehouse and Mad Cow Steakhouse. Meaty with aggressively good reviews.
I'm sure I'm missing at least ten. How does a town this small have so many appealing options?!?! Reply to this email with your Fredericktown recommendations, and I'll put them in the next Fredericktown day trip itinerary. You can bet your buns there will be another one. There's just too much to do (and eat) 'round them parts.
Didja Know?
You’ve likely heard of the famous Appalachian Trail (2,190 miles) and the Pacific Crest Trail (2,650 miles) immortalized in books and film.
But did you know Missouri has its own mini version of a long-distance, thru-hike route?: The Ozark Trail (230 contiguous miles!) stretches from Onondaga Cave State Park to the Eleven Point River. Most thru-hikers tackle it in roughly 2-4 weeks, depending on pace, weather, and how often they stop to spiral.
If you’ve ever thought,“A thru-hike sounds amazing… just not realistic for me,” this might be your trail. It’s right there!...close enough to dream about without quitting your job or disappearing for half a year. Maybe you'll get a book deal and Reese Witherspoon will play you in the movie.
It's also getting outside attention👀. Backpacker Magazine is making a case for backpacking in the Midwest, and Missouri's Ozark Trail made the cut. I mean, we know we're amazing. But it's nice to see others recognizing our cool.
Backroad Weekly is 100% free to read, independently owned, and locally operated (heck, there's just two of us). And we don't want to stuff every issue with ads.
Your contributions go toward scouting trips, research time, writing, and the tools that keep this thing running online. I appreciate any and all support my backroad buds! - Caitlan
The Bootheel Bluegrass Festival is a 3-day indoor banjo-pickin' par-tay. There will be vendors on-site with crafts and baked goods, so you can shop and snack between sets.
Tickets are sold at the door only (no online ticket panic required, yay!).
If you want to make a weekend of it - Special room rates are available. Call Drury Inn (573) 243-9200 to book at the festival rate.
Rock, pick n' roll 🤘
*This week's Featured Event is sponsored by VisitCape
I've been fascinated by the banjo ever since I saw Kermit rock out Rainbow Connection.
To add an event to a future issue, click here, and select Event Ad.
This Weekend’s Happenings
Fri, Jan 30
Indoor Mini Golf Night, Cape Girardeau, MO - Scout Hall turns into a nine-hole indoor mini golf course, complete with a Happy Gilmore-era soundtrack, themed drinks, and door prizes. Choose between two tee times. Dress in your golf attire because you only get one life. Sessions at 6pm-7:30pm and 8pm-9:30pm. $10 advance, $12 day of. 21+ only.
Kirkos and Bonus Sandwich, Cape Girardeau, MO - An evening of experimental music at Spectrum Record Lounge, featuring a St. Louis-based punk jazz trio known for genre-blurring and improv. Music starts at 8pm. $8 cover.
Bootheel Bluegrass Festival, Fruitland, MO - I know I already told you. But I'm telling you again. Memories are short.
The Odd Couple, Anna, IL - A Neil Simon comedy about mismatched roommates, brought to life by the Shawnee Hills Arts Council. 7pm. Tickets $15 for adults, $5 for ages 12 and under.
Writers Club, Murphysboro, IL - A monthly, distraction-free writing hour hosted by the Sallie Logan Public Library. Bring your project and spend some focused time working alongside other writers. Coffee and writing supplies provided. 3pm-4pm.
Coffee on the Cache, Cypress, IL - A laid-back monthly community roundtable at the Cache River Wetlands Center, bringing together neighbors and nature-lovers to swap updates on wildlife sightings, trail conditions, and community ideas. Free coffee and conversation included. 9am-10am.
Sat, Jan 31
LEGO Day, Cape Girardeau, MO - A full day of hands-on LEGO fun for all ages at the Crisp Museum, with open build areas, tower challenges, micro challenges, scavenger hunts, LEGO displays, and register for the hourly LEGO set giveaways. 10am to 4pm. Free and open to the public.
The Pickle Bowl, Cape Girardeau, MO - Day one of a two-day pickleball tournament at The Pickleball Factory, featuring an MLP-style team format, cash prizes, daily raffles, and Super Bowl ambiance. So dress in your Sunday Super Bowl best. $75 per person, $300 per team. (Sponsored)
Winter Tree ID, Cape Girardeau, MO - A guided program at the Cape Nature Center on identifying Missouri tree species beyond their leaves. Learn forestry tidbits and test your skills on an outdoor hike along Ridgetop Trail, weather permitting. Saturday, Jan. 31. 1pm-3pm. Ages 8 and up.
Jase Outdoors Annual Fishing Show, Pilot Knob, MO - A free, public fishing show hosted by Jase Outdoors Bait and Tackle, featuring lure vendors, pro staff tips, live bait displays, raffles, giveaways, and local fishing experts. Food and drinks available. Saturday, Jan. 31. Free admission.
Frosty Brewfest, Ste. Genevieve, MO - An afternoon tasting event at Charleville Brewery & Winery featuring local craft beer, wine, and spirits, plus live entertainment and winter views. VIP tickets include early entry, a souvenir glass, lunch voucher, and event t-shirt. 1pm-5pm. $45 general admission, $85 VIP.
Winter Onesie Bar Crawl, Ste. Genevieve, MO - A cozy-casual bar crawl starting and ending at The Orris on Merchant Street, featuring live music, drinks, prizes, and plenty of onesie fun. I did not realize so many people own a onesie. Wristbands required to win prizes. Check-in begins at 5pm.
Open Craft Sit-In, Burfordville, MO - A relaxed, come-as-you-are crafting meetup at Ava Craft Center. Bring a craft to work on, an appetizer to share, and a drink for yourself, and settle in with fellow makers for a low-pressure afternoon. 11am-2pm.
Southern Illinois Boat and Fishing Show, Marion, IL - Day one of the annual indoor boat and fishing show at The Pavilion, featuring boats, fishing gear, vendors, giveaways, and free seminars. 9am-6pm.
The Odd Couple, Anna, IL - Another chance to see Neil Simon’s comedy about friendship, divorce, and clashing personalities. 7pm. Tickets $15 for adults, $5 for ages 12 and under.
Cold Weather Camping and Hiking 101, Paducah, KY - A free, beginner-friendly class at Hooper’s Outdoor Center covering the basics of camping and hiking safely in cold weather, from proper gear and layering to campsite setup and winter safety, so you don't wind up like Jack Nicholson in The Shining. Free to attend.
Sun, Feb 1
The Pickle Bowl, Cape Girardeau, MO - Championship Day of The Pickle Bowl brings more pickleball, prize money, and raffles as teams compete for rings and the Pickle Bowl trophy. We expect it to get loud and the uniforms to get weird. $75 per person, $300 per team. (Sponsored)
Valentine’s Day Pet Photos, Cape Girardeau, MO - Bring your pet to Busch Pet Products & Care for V-Day photo sessions, with one digital image included and optional prints available. Dress-up encouraged and all pets welcome. $20 per pet.
Southern Illinois Boat and Fishing Show, Marion, IL - The final day of the Southern Illinois Boat and Fishing Show brings more vendors, seminars, and weekend giveaways, plus canned goods collection supporting local pantries. 10am-3pm.
The Odd Couple, Anna, IL - Final performance, following a chaotic roommate dynamic. 2pm. Tickets $15 for adults, $5 for ages 12 and under.
For each event, you’ll find more info at the link. *Events have not been personally vetted because we do not have a time machine or clones.
WORD SCRAMBLE ANSWER: CORNBREAD
Find Us on Social
I talk a lot of crap about social media, but I have to admit that when people respond with comments about how my photos and videos bring back good memories, I'm temporarily, slightly convinced social isn't all that horrendous...but then someone will ask a question that they could just easily Google, and I go back off the rails.
Follow us! Even if it's just to read the wild west known as the "comments" section.
Welp, (*slaps knees), we better get goin'. A big thanks to our sponsor, VisitCape, not just for supporting what we do, but also for sending us fun sponsored sections that people want to read about! How lucky are we to have a sponsor that "gets it"?
Catch you down the road.
Caitlan Hester Publisher, Backroad Weekly
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