I can find something magical about every month in Bend, Oregon, but if you ask my favorite of the twelve, I won’t hesitate to tell you it’s September.

Here’s one of the lovely spots along the Old Mill District where you could be dining if you win!

Summer is still going strong for the first 2/3 of the month, but crowds have thinned out. Our days are still warm enough for floating the river, but our nights are cool enough to make sleeping with the windows open feel blissfully like camping. There are still enough people milling about to create the energetic feel of summer, but you won’t have to fight for a table at your favorite restaurant.

Sounds nice, huh? Here’s what you need to know about visiting Bend, Oregon in September (plus keep reading to win $100 to spend on a fabulous dinner in the Old Mill District!)

What to bring

I’m pretty sure you can manage to round up your own toothpaste and underpants, so don’t use this as an all-inclusive packing list.

September is a great time to play on the Deschutes River in Bend.

But when you plan a September vacation in Bend, here are a few things you should bring:

• Sunscreen. Yep, you still need it (though you can buy it in plenty of places around town if you forget). The sun is still strong, and there’s a good chance you’ll be playing outside, so slather it on and stay safe.
• A bathing suit, a jacket, and a pair of lightweight gloves. I’m lumping these three things together not because you’ll be wearing them all at once (though I’d pay to see a photo of that!) but because it’s important to plan for extreme ends of the weather spectrum when you visit Bend in September. I walked my dog at 6:30 this morning and wished I’d worn a thin pair of gloves to keep my fingers from freezing. By 2 p.m., I was sweltering in 90-degree heat. Here in the mountainous high desert, you have to be ready for anything on the cusp of a season change.
• Golf clubs, kayak, standup paddleboard, bike… You get the idea. This is still the time of year when you want your warm weather toys, so whatever they may be, make sure you toss them in the car.
• A cardigan and a sundress. Er, the male readers may want to skip this one (or not—hey, I’m not here to judge). September is still a terrific time of year to dine outdoors in your strappy little sandals and cute sundress. But if you’re opting for an evening meal outside (like that one you could win in the Old Mill District if you keep reading!) make sure you stash a sweater in your bag. You’ll thank me later.
• Hiking sandals. I know a lot of folks prefer to hoof it in hiking boots year-round, but I’m not one of those people. I live for months where I can comfortably hike in a pair of Keens or Tevas, and September still counts as one of those months. I love the feeling of splashing through a creek and not getting my socks all soggy, and if you’re the same, go ahead and pack the sandals.

For an even better roundup of 10 things you may not know you need to pack for your Bend vacation, check out this blog post.

What to do

You can peruse www.phpstack-307602-2580524.cloudwaysapps.com to find oodles of ideas for activities ranging from arts and culture to restaurants to water recreation to hiking. But for the sake of this blog post, let’s focus on the things you should definitely add to your September agenda:

• 

  Don’t miss your last chance to see a concert at the Les Schwab Amphitheater this season! Tickets are still available for Weird Al Yankovic (Sept. 4) and Ben Harper (Sept. 6).

  Watch a sunset. September is arguably the best time of year to catch dramatic, colorful sunsets in Bend. For ideas on where to get the best view, go here.

• Stroll through Drake Park. The leaves in Bend don’t typically change colors until mid-October, but I’ve heard a few weather geeks predicting it could happen earlier this year. Even if all the leaves are still green and in their proper place on the trees, there are few places on earth more spellbinding than this 13-acre riverfront park in downtown Bend. Walk along the water with a bowl of Bonta Gelato. Hit the Bend Farmers Market on Wednesday for a cornucopia of fresh produce, meats, cheeses, jams, and more.
• Cruise up Pilot Butte. I’m a staunch advocate for traveling on foot to reach the summit of the 500-foot dormant volcano in the middle of Bend, but I know that’s not an option for everyone. Maybe you’re pressed for time, or maybe mobility is limited. Whatever your reason for preferring to drive to the top, September’s a good month to do it. The road closes to motorized vehicles in October, and icy conditions in late-fall or early-winter can make it trickier to hike. One way or another, put Pilot Butte on your bucket list for killer views of the city.
• Catch a concert. The most amazing concert season in Les Schwab Amphitheater history is coming to a close with two remaining shows: Weird Al Yankovic on Friday, Sept. 4, and Ben Harper and the Innocent Criminals on Sunday, Sept. 6. You can still buy tickets here. While you’re at it, take advantage of the chance to dine outside on the riverfront in Old Mill District. You’ll find a roundup of those restaurants here. (Pssst….for a chance to win a $100 to dine in any Old Mill restaurant, follow the directions at the bottom of this post!)

Where to go

Some of Bend’s most popular hotspots are teeming with people in the summer months, so September is your prime opportunity to visit them when the weather’s still great but the crowds have thinned out. Among them:

• Your favorite Bend Ale Trail stop. We have oodles of amazing breweries along the Bend Ale Trail, but there are several where you’ll almost always encounter crowds. That’s especially true in the summer months, but things thin out just a tad when summer ends, making it a little easier for you to nab a seat at Crux Fermentation Project, Worthy Brewing, Deschutes Brewery, and 10 Barrel Brewing. Now’s your chance to claim that outdoor table you’ve been coveting!
  

  September’s a great time of year to nab that coveted outdoor table at popular breweries like Crux Fermentation Project.

• The High Cascade Lakes. Bend locals occasionally fuss if they arrive at popular summer spots like Elk Lake or Green Lake and find hiking trails and picnic areas teeming with people. Thankfully, that tapers off in September, so if you’re hoping for a bit of solitude at a mountain lake without the threat of snow falling, September’s your time to find it.
• Smith Rock State Park. Another Central Oregon hotspot popular with hikers, climbers, sightseers, and birdwatchers, Smith Rock can get a little busy in the summer months. That’s why September makes an extra special time to swing by, with the bonus of offering slightly cooler temps that make it more inviting to wander amid the towering basalt rocks.
• All the hiking trails. Rather than listing them one by one, I’ll just say that all the great hiking trails in Bend and Central Oregon see a slowdown of traffic once September comes, so now’s a great time to cross one off your bucket list. Need ideas? In addition to Visit Bend’s hiking page, the folks at Cascade Hiking Adventures have some terrific suggestions.

Where to stay

One more thing that’s awesome about September? It gets a whole lot easier to get reservations at your favorite hotel, resort, or vacation rental. Go here to start looking!

WIN $100 to dine in the Old Mill District

Another great spot where you could be dining in the Old Mill District.

Want to enjoy a delicious, romantic meal at your choice of restaurant in the Old Mill District? Winning a $100 gift card would be a great way to do that, and you can take your pick of restaurants. Just think….it would be a fabulous date night if you also bought tickets to see Weird Al Yankovic on Sept. 4 or Ben Harper on Sept. 6 at the Les Schwab Amphitheater (you can still buy tickets here).

Comment on this post with one thing from this blog post that you really, really want to do in Bend this September. Better yet, come up with your own! We’ll pick a winner on Wednesday, September 2. Good luck!