When most folks hear "Portland," they immediately think of coffee snobs, rain, and the Pacific Northwest. Honestly? That’s their loss. About 40 miles north of Nashville, tucked right against the Kentucky border, sits the other Portland. Portland, Tennessee. It’s a place where the air smells like strawberries in May and woodsmoke in October. If you’re looking for things to do in Portland TN, you aren’t coming for the light rail or the hipster boutiques. You’re coming for the soul of Middle Tennessee.
The town isn't just a bedroom community for Nashville. It’s got this weird, wonderful mix of hardcore agricultural roots and a surprisingly active local scene. Whether you're a local who has lived here since the 1980s or a traveler passing through on I-65, there's a specific rhythm to this town you've gotta find.
The Strawberry Capital You Probably Ignored
If you visit in May and don't go to the Middle Tennessee Strawberry Festival, did you even visit Portland? I'm serious. This isn't just a small-town fair; it's the town's entire personality. In 2026, the festival is hitting its 85th year on May 9th, and the theme is "Berry Proud to Be an American." It’s basically a massive party celebrating the 250th anniversary of the country.
Expect over 125 vendors. You’ll see a parade that seems to last forever and more strawberry jam than you can physically consume. Most people make the mistake of just showing up for the parade, but the real move is the Strawberry Quilt Show at the Richland Gym (303 Portland Blvd) a few days prior. It’s quiet, impressive, and deeply Southern.
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Beyond the Berry: Farm Life is Real Here
Look, Bottom View Farm is the heavy hitter for a reason. It’s been around for over 67 years. While it’s famous for the pumpkin patch and the "Bottom View Express" train in the fall, it’s actually a year-round operation. They recently reopened a restaurant on-site called The Chew at Bottom View Farm, which does killer catering and classic farm-to-table meals that actually mean something, not just the "fancy" version you see in Nashville.
If you’re traveling with kids, this place is a lifesaver. There's a literal old western town on the property. It’s dusty, it’s authentic, and it keeps them busy while you breathe in some actual fresh air.
Where to Actually Eat (The Locals' Choice)
Portland's food scene is a bit of a sleeper hit. You won't find Michelin stars, but you'll find food that sticks to your ribs.
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- 5 Chefs + The Shoppes at Occasions: This is the "fancy" spot, but in a very cozy, Sweet Southern Eatery kind of way. It’s the place you go for a long lunch when you want actual homemade cake.
- Union Restaurant: If you want American cuisine that feels a bit more modern, go here. Their high-end mac and cheese is basically legendary at this point.
- The Old Spaghetti Factory: Yeah, it's a chain, but the one near Portland is a massive family staple for a reason. The decor is wild.
Honestly, if you're just looking for a quick bite, the local diners near the Portland Historic Business District on Highway 109 are where the real conversations happen. You’ll see farmers talking shop and city transplants trying to figure out the local dialect.
Getting Outside Without the Crowds
Most travel guides will tell you to drive an hour to Mammoth Cave. Sure, the Cedar Sink Trail is great, but you don't have to leave town to get your steps in.
Richland Park is the active hub. It’s got disc golf, soccer fields, and a paved hike/bike trail that’s actually lighted. If you’re more into the "sit on a bench and watch the world go by" vibe, Meadowbrook Park is the winner. It has a dog park, a skate park, and sand volleyball courts.
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For the golfers, Dogwood Hills Municipal Course is surprisingly well-kept for a municipal track. It’s not Pebble Beach, but it’s affordable and usually doesn't have a five-hour round time.
The Historic Soul of Sumner County
The Temple Theatre is the heart of downtown. It’s a timeless gem that still hosts movies and live performances. If you want to feel like you’ve stepped back into 1940, check their schedule.
And don't skip the history. The Portland Historic Business District has markers detailing Confederate invasions and the town’s origins as "Richland Station." If you want the deeper dive, drive a few minutes to Historic Castalian Springs. You’ve got three massive sites there: Cragfont, Wynnewood, and Hawthorn Hill. These aren't just old houses; they are the literal foundations of Tennessee history, with some parts dating back to 1798.
Practical Next Steps for Your Visit
- Check the Calendar: If it's May, book your spot for the Strawberry Festival parade early. If it's October, head straight to Bottom View Farm for the Fall Fest.
- Timing is Everything: Most of the local shops in the historic district close earlier than you'd expect. Aim for a morning or early afternoon stroll.
- Stay Local: If you can, look for a rental in the Sumner County area rather than commuting back to Nashville. The stars are actually visible here.
Portland isn't trying to be cool. It’s just being itself. That’s probably the best thing about it.