Places to visit near Bend, OR?

Hi there! 

Bend is beautiful during May and you will find everything you asked for in the Riverbend Park area...equipment rentals, access to trails, dining ( Greg's Grill & Hola! are my pics) etc.  

Bend also has a number of micro brewery's that serve great food... Cascade Lakes Brewing and 10 Barrel Brewing Company are my pics.  

Downtown Bend has plenty of nice restaurants, sushi, festivals and neat shops... 

If you get a chance, try Togo to Sunriver for a hike...a great little resort town by Bend. 

Also...I've skid Mt Bachelor in May many times... 

Hope this helps! 

Cheers 

Mike

It's been a few years since I went to Bend, but I have fond memories of a couple of spots.

One is Deschutes Brewery. Mirror Pond and Black Butte Porter were basically the official beers of my grad school education in Eugene, OR. When you can drink them at the source, you should! Here's the Deschutes website. 

I also explored a lava tube that I think was Lava River Caves. It was incredibly interesting, so it's a cool place for an exploratory hike and taking photos. It's not where you go for a workout. 

You will want to pay attention to the water levels in the Deschutes in downtown Bend. There is some controversy over a dam here and they've been saying all winter that the river levels in downtown could be to low to float this summer.  Tumalo Creek Kayak & Canoe (Tumalo Creek Kayak and Canoe) in the Old Mill District would know best. There's also Wanderlust Tours who offer various guided activities in and around Bend.

Don't miss hiking and even rock climbing (hire a guide) at Smith Rock State Park - really amazing rock formations there! There is a marina at Lake Billy Chinook at the Cove Palisades State Park (Cove Palisades State Park) that rents various watercraft (unless you have a high clearance, 4-wheel vehicle it's not advised to try to drive past the end of the pavement towards Sisters!).

There aren't really wine tasting rooms in Bend but there are plenty of breweries! Check out the Bend Ale Trail for a full listing - the ones that make my can't miss list are 10 Barrel Brewing Company (10 Barrel) and Crux Fermentation Project (Crux go for sunset!) - both also have good food. Restaurants we like are Jackson's Corner (Jackson's Corner West Side for breakfast & lunch), Chow (Chow breakfast / brunch), 900 Wall (900 Wall), Noi (Noi), Barrio, BrickHouse (Brickhouse), Jackalope Grill (Jackalope Grill)...

Hi, Bend is an awesome town.  I've called Bend home for 5 years now.  It is pretty awesome.  For kayaking and Biking there are two shops that I would recommend.   Tumalo Creek Kayak & Canoe and Canoe in the Old Mill District is the place to get set up with your on water gear for tubing, Stand Up Paddle Boarding, or Kayaking.  It's a great place, and they're right on the river.  For bike rentals check with Pine Mountain Sports on Century Drive.  If I'm limited on time the one hike I would be sure to do is Tumalo Falls.  You can find directions at Visit Bend downtown for this hike, and tons of others.  Three places I can recommend for Breakfast are Cafe Sintra downtown (my favorite), Jackson's Corner between downtown and the Old Mill district, and Chow on Newport Ave.  For Dinner,  there are a number of different options, Zydeco Kitchen & Cocktails, 900 Wall, The Blacksmith Restaurant, Bar & Lounge, Spork, and Wild Rose Northern Thai Eats are some of my favorites.  Enjoy your trip, and have fun.