Blog Comparisons & rankings

2026-02-035 min readcheaphotels

Seven Middle Tennessee courthouse squares and Main Streets ranked on how much is actually open when you get there.

1. Springfield's own Main Street and courthouse square

Start honest: Springfield's square is the best in the immediate area, and it isn’t a home-town bias call. The 1879 Robertson County Courthouse anchors a walkable block with 30-plus occupied storefronts, four independent coffee spots, a working hardware store, and a Saturday farmers market from May through October. Parking is free and unrestricted around the square. The recent facade grants have brought back second-floor windows on buildings that were bricked up for 40 years.

What lands it first: nearly everything is open Tuesday through Saturday, not just weekends. Bam Nutrition, Yellow Door Coffee, and a handful of lunch spots run real weekday hours because the courthouse business supports them. Give it a half day, park once, and you can eat two meals and browse without moving the car. If you’re staying in Springfield, this is your evening walk. Skip only if you specifically want antiques-heavy shopping, which several of the smaller towns below do better.

2. Adams — tiny, weird, and completely committed

Adams has maybe 600 residents and three blocks of Main Street, and it punches far above its size because the whole town leans into the Bell Witch story without becoming a theme park about it. The old Bell School is now a museum, the post office is genuinely from another century, and the two general-store-style shops sell local sorghum, cured hams, and books about the haunting. It's 15 minutes northwest of Springfield on Highway 41.

Give it an hour on its own or 90 minutes if you’re pairing it with the Bell Witch Cave farm two miles south. The catch: several storefronts only open Friday and Saturday, and there is no coffee shop, so caffeinate before you arrive. Ranked second because the density of real, non-generic experience per block is higher than anywhere else on this list. It's the antidote to a strip-mall afternoon.

3. Cross Plains — the crossroads that stayed

Cross Plains sits on Highway 25 about 20 minutes northeast of Springfield and is best known for Thomas Drugs, a working pharmacy with a functioning soda fountain that has been in the same family since 1911. Order a phosphate or a hand-scooped milkshake and sit at the counter. Around it are a handful of antique shops, a tiny museum in the old bank building, and the crossroads that give the town its name.

Go on a Saturday between 10am and 2pm when everything is open. Give it 90 minutes plus the drive. The town is genuinely small — you’ll exhaust the browsing quickly — but the soda fountain by itself justifies the trip and the lunch counter does a passable BLT for under ten dollars. Ranked third because the anchor is exceptional and the surrounding blocks have enough to fill a morning, but weekday hours are thin outside Thomas Drugs.

4. Portland — bigger, working, worth the drive

Portland is 25 minutes northeast on I-65 and has a genuine downtown grid rather than a single square. The Strawberry Festival in May puts it on the regional map, but the year-round appeal is a mix of a working hardware store, two decent lunch counters, a couple of thrift and vintage shops, and the small railway museum in the old depot. It feels like a town that still uses its downtown for daily errands, which is rarer than it should be.

Give it two hours. Come Tuesday through Saturday. The catch is that Portland's downtown is spread over four or five blocks rather than one dense square, so it walks longer than it looks on a map. Pair it with a stop at Long Hungry Creek Farm or one of the roadside produce stands on the way back to Springfield in summer. Ranked fourth because it's substantial but requires more planning than the tighter squares above.

5. Ashland City — river town, real lunches

Ashland City sits on the Cumberland River about 35 minutes southwest of Springfield and has a compact Main Street that runs down to the water. The Riverbluff Grill does honest catfish plates for around 16 dollars with a river view, and the Cumberland River Bicentennial Trail starts nearby if you want to walk off lunch on a rail-trail through cypress. The town square proper is small but has a used bookshop and a coffee spot.

Give it half a day if you’re combining the trail with lunch. The reason it ranks fifth rather than higher: the downtown itself is thinner than Adams or Cross Plains, and much of what makes Ashland City worth the drive is the river and the trail rather than the storefronts. If you want a walk-plus-meal outing and you’ve done Springfield's square already, this is the pick.

6. Pleasant View — small but improving

Pleasant View is 20 minutes west of Springfield on Highway 49 and has been rebuilding its Main Street presence for about a decade. There's a good breakfast spot, a coffee house that roasts its own, and a couple of gift and home shops in restored buildings. It doesn’t have the density of Cross Plains or the character of Adams, but it's genuinely pleasant to walk on a Saturday morning and hasn’t been hollowed out.

Give it an hour, maybe 90 minutes with breakfast. The trajectory is upward — new tenants in the last two years — but you’re arriving mid-story rather than at a finished destination. Ranked sixth because a visit is worthwhile but doesn’t stand alone; pair it with a drive out to Ashland City or a hike at Cheatham Wildlife Management Area to make a full day of it.

7. White House — the honest bottom of the list

White House is 20 minutes east of Springfield and has a small historic core near the old inn site that gives the town its name. The White House Inn Library and Museum in the reconstructed inn is a decent 30-minute stop, and there are a couple of restaurants in the surrounding blocks, but the town's centre of gravity has moved to the I-65 exit and the retail strip, which is not what anyone means when they ask about a Main Street.

Include it only if you’re already driving Highway 31W or heading to Nashville. Give the museum half an hour and don’t build a trip around it. Ranked last because being honest about the list matters more than padding it: five of the towns above will give you a good half-day, White House gives you a solid 45 minutes and a strip mall. That's still worth naming, but not worth pretending otherwise.

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Before you book

The questions people ask about Cross Plains, answered with this month’s numbers.