🧭 Hundred-Mile Happenings: Hamilton County Fair, Boo on the Block, Jasper Jack-O-Lantern Jamboree and Ringgold Hayrides

Or: Free Trunk-or-Treats, a Cookeville Homeschool Market, Soddy-Daisy Craft Fair and Merry Market — Eight New Day Trips Within About 100 Miles of Dunlap

Howdy, neighbor. Here’s batch number sixteen of Hundred-Mile Happenings, our running list of unusual, family-friendly outings within about 100 miles of Dunlap. As always, we lay it out plain: when, where, how far, what it costs and who’ll love it. And as always, no repeats. Every one of these is new to the list.

This round stretches from a North Georgia depot hayride to a Sale Creek county fair with fireworks: Ringgold’s Haunted Depot weekends (with an all-ages hayride and bonfire if the haunted house isn’t your style), a free Trunk or Treat Extravaganza at Central Church of Christ, Cookeville’s Homeschool Vendor Market where kids become the shopkeepers, free Boo on the Block on West 14th in Chattanooga, Jasper’s Joshua K. Jennings Jack-O-Lantern Jamboree 5K on Courthouse Square, the Little Debbie Hamilton County Fair at McDonald Farm, a Family Fall Craft Fair in Soddy-Daisy, and Merry Market at St. Thomas Aquinas in Cookeville.

⏱️ Your 30-second trip list

• Fri.–Sat. nights Oct. 16–17, 23–24, 30–31, 7–11 p.m. Eastern: Ringgold Haunted Depot — hayride about $5; haunted house $15; combo about $23.
• Sun., Oct. 25, 6:30–8:30 p.m. Eastern: Trunk or Treat Extravaganza, Central Church of Christ, Chattanooga. Free.
• Sun., Oct. 25, noon–4 p.m. Central: Fall Festival & Homeschool Vendor Market, Putnam County Fairgrounds, Cookeville. Free.
• Sat., Oct. 31, 10 a.m.–2 p.m. Eastern: Boo on the Block, 71 W. 14th St., Chattanooga. Free.
• Sat., Oct. 31, 9 a.m. Central (5K): Jasper Jack-O-Lantern Jamboree 5K, Courthouse Square. About $25; afternoon square fun — check with Town of Jasper.
• Fri.–Sun., Nov. 6–8: Little Debbie Hamilton County Fair, McDonald Farm, Sale Creek. Advance 3-day about $16 adult; kids 10 & under free.
• Sat., Nov. 7, 9 a.m.–4 p.m. Eastern: Family Fall Craft Fair, Holy Spirit Catholic Church, Soddy-Daisy. Free to browse.
• Fri.–Sat., Nov. 20–21: Merry Market, St. Thomas Aquinas, Cookeville. Free admission.

🕰️ The one thing to remember: the time line. Chattanooga / Hamilton County (Boo on the Block, Trunk or Treat Extravaganza, Hamilton County Fair in Sale Creek) and Ringgold / Catoosa County, Georgia, are on Eastern Time, one hour ahead of us. So a 10 a.m. Eastern Boo on the Block start is 9 a.m. our time, and a 7 p.m. Eastern Ringgold hayride is 6 p.m. our time. Jasper / Marion County and Cookeville / Putnam County are on Central Time, same as Dunlap. Soddy-Daisy sits in Hamilton County on Eastern. And remember, clocks fall back on Sunday, Nov. 1 — after that, Eastern is still one hour ahead.

🚂 Hayrides, Bonfires and Optional Frights in Ringgold

The Ringgold Haunted Depot takes over the historic depot on Friday and Saturday nights for three October weekends. If jump-scares aren’t your cup of coffee, you can still make a night of it: an all-ages hayride on the nature trail, a downtown ghost tour, a bonfire with s’mores and live music on the grounds. The haunted house is there for the thrill-seekers; the hayride and bonfire are there for everybody else. Cousin Billy would call that “pick your own scare level.”

Why it’s worth the drive:

• When: Fri.–Sat., Oct. 16–17, 23–24, and 30–31, 2026, 7–11 p.m. Eastern (6–10 p.m. our time). Live music each weekend (Lovelace; Courtney Daly & the Daly Grind; PLVNET — check listing for which nights).
• Where: Historic Ringgold Depot, about 155 Depot St., Ringgold, GA 30736.
• How far: About 35–40 miles, roughly 45–55 minutes.
• Cost: Haunted Depot about $15; Ghost Tour about $7; Hayride about $5; combo for all activities about $23. Tickets sold in person at the event per organizer listing.
• Who’ll love it: Families who want a hayride without a full haunted-house commitment, teens who want the frights, and anyone who likes live music by a bonfire.
• Good to know: Eastern Time. Free public parking near City Hall, Market Way, Mountain Street and Nashville Street. Front Porch Fridays at Benton Coal (free acoustic music 6–8 p.m.) sits just down Depot Street if you arrive early. Keep little ones on the hayride/bonfire track if the haunted house is too much — check before you go for age guidance on each attraction.

👉 Read more (Ringgold Haunted Depot)

🍬 A Parking-Lot Candy Parade on Vine Street

Central Church of Christ’s Trunk or Treat Extravaganza fills a well-lit parking lot with decorated trunks, mountains of candy, drinks, food trucks, music and on-site security. Free, open to the public and built for early-evening costumes — the kind of Sunday night that gets the kids home before the late news.

Why it’s worth the drive:

• When: Sun., Oct. 25, 6:30–8:30 p.m. Eastern (5:30–7:30 p.m. our time).
• Where: Central Church of Christ, 400 Vine Street, Chattanooga, TN 37403.
• How far: About 35 miles, roughly 45–55 minutes.
• Cost: Free.
• Who’ll love it: Costume kids, grandparents who prefer pavement to dark trails and families stacking a quiet Sunday treat stop.
• Good to know: Eastern Time. Same calendar day as Cookeville’s Homeschool Vendor Market — morning plateau shopping and evening Chattanooga candy is a long stack; most folks should pick one. Bring a bag and a light jacket. Confirm any last-minute changes on the Choose Chatt / Facebook event link.

👉 Read more (Trunk or Treat Extravaganza — Choose Chattanooga)

🧒 Kids as the Shopkeepers in Cookeville

The 4th Annual Fall Festival & Homeschool Vendor Market flips the usual craft fair: more than 50 homeschool kids set up their own booths with ornaments, woodworking, crochet, baked goods, toys, jewelry, candles and more. Free admission, free family fun (photo area, live music, bounce houses, kids’ activities) and food trucks — a plateau afternoon that cheers on young makers instead of just shopping past them.

Why it’s worth the drive:

• When: Sun., Oct. 25, noon–4 p.m. Central.
• Where: Old Putnam County Fairgrounds, 155 Fairground Ln., Cookeville, TN.
• How far: About 55–60 miles, roughly 1 hour–1 hour 15 minutes.
• Cost: Free admission (food trucks and vendor purchases extra).
• Who’ll love it: Families who want to encourage kid entrepreneurs, early Christmas shoppers and anyone who likes a fairgrounds stroll without a ticket booth.
• Good to know: Central Time. You do not have to homeschool to attend — organizers welcome the whole community. Bring cash and a tote. Same Sunday as Trunk or Treat Extravaganza — pick plateau makers or Chattanooga candy, not both unless stamina is high.

👉 Read more (Fall Festival & Homeschool Vendor Market)

🎉 Free Boo on the Block on West 14th

First Things First’s Boo on the Block is a free Halloween community block party across from the Choo Choo: crafts, inflatables, a live DJ, snacks, giveaways and local businesses opening their doors with specials. No ticket, no scare maze — just costumes and a neighborhood afternoon aimed at families who need an easy win.

Why it’s worth the drive:

• When: Sat., Oct. 31, 10 a.m.–2 p.m. Eastern (9 a.m.–1 p.m. our time).
• Where: 71 W. 14th St., Chattanooga, TN 37408 (West 14th Street neighborhood near the Choo Choo).
• How far: About 35 miles, roughly 45–55 minutes.
• Cost: Free.
• Who’ll love it: Younger kids who fade by supper, grandparents who want daylight Halloween and anyone already downtown for the Choo Choo.
• Good to know: Eastern Time. Daytime slot pairs well with an evening plan elsewhere — or keep the whole day gentle. Already-covered Truck-or-Treat at the Towing Museum and Cleveland’s Halloween Block Party are later the same day; don’t stack three candy stops. Confirm details closer to Oct. 31 via First Things First / Chattanoogan coverage.

👉 Read more (Boo on the Block — First Things First)

🏃 Jack-O-Lanterns on Jasper’s Courthouse Square

The Joshua K. Jennings Jack-O-Lantern Jamboree 5K Fun Run and Walk starts on Jasper Courthouse Square Halloween morning — a hometown race named for the event’s founder, with shirts while they last. In recent years the Town of Jasper and Lions Club have followed the 5K with a free afternoon of trunk-or-treat, games, petting zoo and costume contests on the square. The 2026 5K is confirmed; call City Hall to confirm afternoon hours before you pack the costumes.

Why it’s worth the drive:

• When: Sat., Oct. 31, 2026. 5K historically 9 a.m. Central on Courthouse Square (confirm race-day start on Active.com). Afternoon square festivities in prior years ran about 4–8 p.m. Central — check with Town of Jasper before you go.
• Where: Marion County Courthouse Square, Jasper, TN 37347.
• How far: About 18–22 miles, roughly 25–35 minutes.
• Cost: 5K about $25 via Active.com (day-of signup often available). Afternoon trunk-or-treat has historically been free (food purchases extra).
• Who’ll love it: Local runners, costume families and anyone who wants Halloween without leaving the Valley.
• Good to know: Central Time. Closest outing on this list. Questions: Jasper City Hall (423) 942-3180 / (423) 942-3810. Same day as Boo on the Block — morning Jasper and midday Chattanooga is doable if you leave the square on time.

👉 Read more (Jasper Jack-O-Lantern Jamboree 5K)

🎡 Little Debbie Hamilton County Fair at McDonald Farm

The Little Debbie Hamilton County Fair returns to the 2,100-acre McDonald Farm in Sale Creek for Veterans Day weekend — rides (Ferris wheel included this year), Outlaw Rodeo, lumberjack shows, pig races, ag exhibits, craft vendors, fair food and fireworks. Saturday headliner is country star Rodney Atkins with Brandon Davis; Sunday’s “Faith on the Farm” features David Leonard and Amber Carrington. Passes cover rides, concerts, rodeo and shows — the rare county fair where the ticket isn’t a death-by-a-thousand-wristbands.

Why it’s worth the drive:

• When: Fri.–Sun., Nov. 6–8, 2026 (Veterans Day weekend). Full daily schedule on hamiltontnfair.com — check set times for concerts, rodeo, lumberjacks and fireworks before you go.
• Where: McDonald Farm, 16705 Coulterville Road, Sale Creek, TN 37373.
• How far: About 25–30 miles, roughly 35–45 minutes.
• Cost: Advance three-day about $16 adult / $14 ages 11–17; gate three-day about $19 adult. Daily about $12 adult / $10 ages 11–17. Kids 10 and under free. Senior / military / first responder / teacher discounts at the gate with ID. Parking free. Buy ahead at hamiltontnfair.com.
• Who’ll love it: Multi-generation families, rodeo fans, ride kids and anyone who wants a real farm fair without inventing a Nashville weekend.
• Good to know: Eastern Time (Hamilton County). Rain or shine; severe-weather updates on the fair site/social. Collapsible lawn chairs OK; leave pets at home (service animals welcome). Same weekend as already-covered Cowan craft show and Mistletoe Market — you don’t need every Nov. 6–7 outing. Artists and times subject to change — confirm before purchase.

👉 Read more (Hamilton County Fair) · FAQ & tickets

🧵 Family Fall Craft Fair in Soddy-Daisy

Holy Spirit Catholic Church’s Family Fall Craft Fair fills a Saturday on Dayton Pike with vendors and fall browsing — a simple Soddy-Daisy stop if you’re already near the Hamilton County Fair weekend or just want handmade gifts without a downtown parking hunt.

Why it’s worth the drive:

• When: Sat., Nov. 7, 9 a.m.–4 p.m. Eastern (8 a.m.–3 p.m. our time).
• Where: Holy Spirit Catholic Church, 10768 Dayton Pike, Soddy-Daisy, TN 37379.
• How far: About 30–35 miles, roughly 40–50 minutes.
• Cost: Free to attend (vendor purchases extra). Vendor contact listed as Debbie Newman (770) 722-0957 for booth questions.
• Who’ll love it: Craft shoppers, early Christmas buyers and families stacking a quieter morning before a fair afternoon in Sale Creek.
• Good to know: Eastern Time. Same Saturday as Hamilton County Fair Day 2 (Rodney Atkins night) — morning crafts and afternoon/evening fair is a natural stack if energy holds. Confirm hours closer to Nov. 7 if the listing updates.

👉 Read more (Family Fall Craft Fair — Soddy-Daisy)

🎄 Merry Market Kicks Off Christmas in Cookeville

St. Thomas Aquinas Merry Market turns the parish hall into an indoor Christmas market: local vendors, handmade gifts, décor, jewelry, apparel, hot chocolate and baked goods. Free admission, two days, whole community welcome — a calm way to start the Christmas list before the malls get loud.

Why it’s worth the drive:

• When: Fri., Nov. 20, 5–8 p.m. Central and Sat., Nov. 21, 9 a.m.–2 p.m. Central.
• Where: St. Thomas Aquinas Catholic Church Parish Hall, 421 N. Washington Ave., Cookeville, TN 38501.
• How far: About 55–60 miles, roughly 1 hour–1 hour 15 minutes.
• Cost: Free admission.
• Who’ll love it: Early Christmas shoppers, grandparents hunting handmade gifts and anyone who prefers indoor browsing when November wind picks up.
• Good to know: Central Time. Same Saturday as already-covered Christmas on the Square in Cleveland and Touch-a-Truck — pick one holiday kickoff. Bring a tote and a list. Vendor weekend fee is about $40 if you want a booth — email the parish events address listed on the AllEvents page.

👉 Read more (Merry Market — St. Thomas Aquinas)

🗓️ Put These on the Fridge

• Oct. 16–17, 23–24, 30–31 evenings Eastern: Ringgold hayride (~$5) or full combo (~$23).
• Sun., Oct. 25, noon Central: Free Homeschool Vendor Market, Cookeville.
• Sun., Oct. 25, 6:30 p.m. Eastern: Free Trunk or Treat Extravaganza, Vine Street.
• Sat., Oct. 31, 9 a.m. Central: Jasper Jack-O-Lantern 5K (~$25); confirm afternoon square fun.
• Sat., Oct. 31, 10 a.m. Eastern: Free Boo on the Block, West 14th.
• Nov. 6–8: Hamilton County Fair at Sale Creek — buy passes ahead; kids 10 & under free.
• Sat., Nov. 7, 9 a.m. Eastern: Family Fall Craft Fair, Soddy-Daisy.
• Nov. 20–21: Free Merry Market, Cookeville.

✅ Trip-planning checklist

• ✅ Pick one Oct. 25 plan and one Oct. 31 plan first — candy and craft fairs stack faster than leftover chili.
• ✅ Write the time zone on the fridge sticky: Eastern for Chattanooga, Sale Creek, Soddy-Daisy and Ringgold; Central for Jasper and Cookeville.
• ✅ Buy Hamilton County Fair passes online before Veterans Day weekend.
• ✅ Register for the Jasper 5K on Active.com if you’re running; call City Hall about afternoon trunk-or-treat.
• ✅ Pack a tote, a light jacket, cash for food booths and hayride tickets (Ringgold sells on site).
• ✅ Check the sky and the organizer page the morning of — fall weather changes fast.
• ✅ After Nov. 1, remember clocks fell back — Eastern is still one hour ahead of Dunlap.

Remember: unusual beats generic, free beats fancy when the kids are happy, and a day trip should still get you home for leftover pie.

— Dunlap.Today

❓ Frequently Asked Questions

Are these events already on earlier Hundred-Mile Happenings lists?

No. We keep a covered-events list and skip anything we’ve already featured. This batch is all new names for article #16.

Is the Ringgold Haunted Depot too scary for little kids?

The haunted house is optional. Organizers also offer an all-ages hayride, bonfire with s’mores and live music — start there and skip the fright rooms if anyone’s nervous.

Which Oct. 31 outing should we pick?

Morning Jasper 5K (and square fun if confirmed), midday Boo on the Block, and already-covered evening options (Towing Museum Truck-or-Treat or Cleveland Block Party) is the ambitious stack. Most families should pick one candy plan and save energy for costumes.

Do we need tickets for the craft shows and block parties?

Trunk or Treat Extravaganza, Homeschool Vendor Market, Boo on the Block, Family Fall Craft Fair and Merry Market are free to attend. Jasper 5K needs a ~$25 registration. Hamilton County Fair needs a paid pass (kids 10 & under free). Ringgold attractions are priced per activity at the gate.

Eastern or Central — which clock do I set?

Dunlap / Sequatchie is Central. Chattanooga, Sale Creek, Soddy-Daisy and Ringgold run Eastern (one hour ahead). Jasper and Cookeville match us on Central.

How do you pick these events?

We look for one-of-a-kind, family-friendly outings within about 100 miles of Dunlap, and we check each one against the organizer’s own page whenever we can. We keep a list so we never repeat an event. If you know a hidden gem, tell us at Dunlap.Today.

🔗 Other Resources

• Little Debbie Hamilton County Fair
• Hamilton County Fair FAQ & tickets
• Hamilton County Parks — Fair page
• Boo on the Block (First Things First)
• Trunk or Treat Extravaganza — Choose Chattanooga
• Ringgold Haunted Depot
• Jasper Jack-O-Lantern Jamboree 5K
• Fall Festival & Homeschool Vendor Market (Cookeville)
• Family Fall Craft Fair (Soddy-Daisy)
• Merry Market — St. Thomas Aquinas
• Choose Chattanooga: Events calendar
• National Weather Service Morristown: Valley forecast
• Dunlap.Directory: Local businesses for gas, food and supplies

🍂 Slow Down and Go See Something

You don’t have to invent a big vacation to make a fall memory. From a Ringgold hayride to free trunk-or-treats, a Cookeville kids’ market, Boo on the Block, Jasper’s square, a Sale Creek county fair with fireworks, Soddy-Daisy crafts and an indoor Merry Market, every outing on this list is within about an hour and a half of home — and several are under forty-five minutes. Grab a buddy, check the clock and the sky, and go.

Keep exploring, keep it easy and keep reading. Read Dunlap.Today for more Hundred-Mile Happenings, and find the Valley businesses that’ll fuel your trip on Dunlap.Directory.