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5 neighborhood side trips to explore in Bend

Drake Park Fall Bend Oregon

If you’ve vacationed in Bend a time or two, odds are good you’ve hit all the major tourist attractions. Drake Park, a hike to Tumalo Falls, maybe a river float or a visit to Mt. Bachelor.

While those things should be on every visitor’s Bend bucket list, it’s fun to venture outside the Westside core surrounding Downtown Bend and the Old Mill District. Here are five zones worth exploring, along with what you should see, do, and eat while you’re there!

Start your NW Crossing adventure with a made-to-order lunch at Poke Row.

Northwest Crossing

Still technically part of Bend’s Westside, the Northwest Crossing neighborhood is one you’re not likely to stumble upon unless you go there for something specific like a festival or Farmers’ Market.

But the abundance of cute shops and fabulous restaurants (not to mention a homey, cozy vibe) makes the Northwest Crossing neighborhood worth a visit.

Pretty Compass Park makes a lovely stroll.

Grab a tasty, custom-made-just-for-you lunch at Poke Row before strolling a couple blocks for a loop around Bend’s uniquely round Compass Park.

Tasty bruschetta and lemony Caesar at Portello.

On your return trip back, browse cute clothing and home décor shops, and maybe pop into Look! Salon for a pedi or Love Your Skin for a pampering facial.

When happy hour rolls around, pick a cozy patio table beside the heater at Portello Winecafe (or duck inside if the weather is chilly). Fortified by their scrumptious bruschetta, their to-die-for lemony Caesar, and a good glass of wine, stroll around the corner to Roundabout Books to grab a cup of coffee and some vacation reading.

When dinner rolls around, Washington and La Rosa are both excellent choices. Now you’re feeling like a local!

Visit The Barrel Thief for a tour of Oregon Spirt Distillers and a chance to sample their handmade cocktails.


The Makers District

More of an industrial area than an actual neighborhood, Bend’s Makers District is worth a visit for those intrigued by locally-owned shops, handmade goods, and tucked-away restaurants only the savviest local foodies have discovered.

The Makers District spans First and Second Street between Greenwood and Olney. A good starting point is Silver Moon Brewery for a pint of tasty craft beer and some local music. Just a few doors down, nab tickets to see a play at 2nd Street Theater.

Your life isn’t complete until you’ve added soy-brined duck egg to your ramen bowl at 123 Ramen

Meander shops like Natural Edge Furniture and Bend Velo Bike Shop to work up an appetite. For one of the tastiest lunches in town, order a freshly-made combo bowl at 123 Ramen. Add on a soy-brined duck egg and a side of fresh rolls and be prepared to swoon.

When cocktail hour rolls around, hit Oregon Spirit Distillers for a distillery tour and samples of handmade cocktails and spirits.

The rooms at Wall Street Suites make a great home base for exploring the Makers District.

Then walk it off with a stroll back toward Downtown Bend to explore Pioneer Park (the quieter, quainter cousin of popular Drake Park. Bonus: You’ll be right next to Wall Street Suites, which makes a terrific home base for those who appreciate chic luxury and the sort of creative reinvention that characterizes much of the Makers District.



The term “Mid-Town” is one you’ll rarely hear from anyone but Bend locals, but it’s a vibrant, scenic Bend district you’ll pass through on your way to hike Pilot Butte (which you’re planning anyway, right?)

No trip to Bend is complete without a hike up Pilot Butte (which is a great addition to your exploration of Mid-Town).

Mid-Town encompasses the blocks roughly between Pilot Butte and the Bend Parkway north of Franklin Avenue. It’s comprised of an eclectic mix of neighborhoods, shops, and did I mention the killer views of (and from the top of) Pilot Butte?

Technically on the cusp of Mid-Town is Easy Float, so stop here early in your journey for a relaxing float to get you primed for vacation mode.

Cocktails and nibbles at Rockin’ Dave’s Backporch.

Once you’re feeling chill, head to Rockin’ Dave’s for one of the best breakfast sandwiches in town (the Clogger is one of my favorites). If it’s later in the day, meander around to the other side of the building for cocktails and tasty eats in a tucked-away corner at Rockin’ Dave’s Bistro & Backstage Lounge.

Want the best breakfast burritos (or the best burritos PERIOD) in Bend? Los Jalapeños is a must-try any time of day, with super-cheap happy hour specials that come with a bonus margarita.

If you’re looking for unique shops, this stretch of Greenwood boasts plenty of them, including The Reptile Zone and multiple thrift stores for bargain hunters seeking everything from clothing to furniture.

Oh, the things you’ll see in Mid-Town (aka scenes from The Reptile Zone).

Pro tip: If Westside favorites like Parilla Grill and Croutons are on your list but you’ve shied away from the long lines, you’ll be happy to know both places have Mid-Town locations that are less crowded than their Westside counterparts with the same great food.

Want to visit one of the prettiest parks in Bend? Try Hollinshead Park with its picturesque barn and rich history as a former homestead.


Northeast Bend

Full disclosure: This is my neck of the woods, and I’ll admit there’s a part of me that wants to keep it all to myself.

Worthy Brewing is a magical NE Bend stop.

But I’d be a jerk not to tell you that Northeast Bend is the gateway to one of my favorite places to explore, the Oregon Badlands Wilderness. Remember what I said earlier about Westside hotspots adding second locations in quieter parts of town? Fuel up for your Badlands adventure with a hearty breakfast at Jackson’s Corner Eastside, which gives you a chance to cross one of Bend’s most popular eateries off your list in a quieter space.

Once you’ve gotten your fill of outdoor recreation in the Badlands, stop at Worthy Brewing for a pint, some of their killer fish tacos, and a chance to explore their legendary Hopservatory.

If you have Rover in tow, don’t miss the Bob Wenger Memorial Off-Leash Area in Northeast Bend.

This is only the tip of the iceberg for the beer scene in Northeast Bend. Monkless Belgian Ales, Craft Kitchen & Brewery, and Bridge 99 Brewery are nicely positioned for a mini-walking tour of some of the Bend Ale Trail’s more tucked-away breweries. You can finish things off at 10 Barrel’s Eastside pub with a pizza and pint next to one of their fire pits.

Oh, and if you have your pup in tow, don’t miss the chance to visit Bend’s largest dog park, the 18-acre Bob Wenger Memorial Off-Leash Area. It features grassy fields, meandering trails, and a spray park for pups who love water.


Business 97 (aka 3rd Street)

Those of us who’ve been in Bend a long time remember the pre-Parkway days when Highway 97 (aka. 3rd street) was the only way to travel between Bend’s north and south ends. But times have changed, and while 3rd Street is no longer the speediest way to make the north/south trek, it’s a great chance to scope out businesses and eateries you might not discover in a rush from one end of town to the other.

Tomo Sushi is one of countless amazing eateries along Highway 97 (also known as 3rd Street).

On the north end of town, you’ve got the Cascade Village Shopping Center with recognizable chains like Trader Joe’s, Best Buy, and Dick’s Sporting Goods (sprinkled with some locally-owned shops and eateries). On the south end are the Bend Factory Stores, and besides offering killer bargains at outlet shops like Coach and Columbia, it’s also home to renowned farm-to-table dining at Wild Oregon Foods.

Your best bet is to make a deliberately slow journey between the two ends, discovering eateries along the way like El Sancho (OMG, the tacos!) and Laughing Planet (a good option for vegans and gluten-free diners). Tomo Sushi on the far south end is another terrific choice.

Want to pick up a permanent souvenir in tattoo form? Pre-book your appointment at Monolith Tattoo, one of Bend’s best-known tattoo shops. While you don’t want to combine inking and toking, you’ll find an abundance of marijuana dispensaries along this same stretch of 3rd Street.

Rooms with killer views of the Deschutes River are a perk at Riverhouse on the Deschutes (also on Highway 97).

Bonus: Your slow trek along 3rd Street is a pleasant way to get to the offices of Wanderlust Tours, where you can book all the canoeing, caving, snowshoeing, and brewery adventures your little heart desires.

Extra bonus: Heading south is a great way to access some pretty terrific hiking and exploring like Bessie Butte and the Newberry National Volcanic Monument, not to mention the High Desert Museum.

One more bonus: Some of the most budget-friendly lodging in town can be found along this 3rd Street corridor. You’ll also find Riverhouse on the Deschutes, which has awesome on-site food and perks like  indoor/outdoor pools and river views.

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