May is beautiful in Bend, Oregon! Here at Pronghorn Resort we are enjoying longer days, gorgeous sunsets, great golf conditions, and awesome mountain biking weather. With the budding trees and blooming daffodils comes a ton of fun things to do! You’ll find outdoor concerts, running and cycling races, Mother’s Day and Memorial Day events, and Mt. Bachelor’s closing weekend.

If you find yourself in Bend in May, lucky you! As the unofficial start to summer, Memorial Day Weekend is an amazing time to visit with so much to see and do. The rest of the month is just as entertaining. Bend’s unique high desert climate and proximity to Mt. Bachelor means you can ski in the morning and golf in the afternoon. When you’re not on the mountain or on the course, take a peek at our resort events and activities and our list of best Bend events in May below. 

Be sure to save some time for a sunset soak in the heated pool and hot tub, open year-round, right here at the Huntington Lodge!


Start planning your Bend vacation now because there’s always a popular reason to visit this cool Oregon town.

Concert Season Heats Up at Les Schwab Amphitheater

Plan a trip around a show at Bend’s favorite summer concert venue, Les Schwab Amphitheater. Check the latest concert lineup and make plans for a beautiful evening of live music on the lawn. The riverside Amphitheater presents some of the biggest names in entertainment and May is when the stage starts to heat up for summer.

First Friday Art Walk 

View sensational local and national art at dozens of downtown Bend businesses on the first Friday of every month. Stroll through the streets and take in art exhibit openings, artist talks, live music, wine and food, and more. This monthly event is free, and shops stay open later than usual. Pair it with dinner at 900 Wall or Bos Taurus for a night full of culture, friends and food!

Mother’s Day Brunch at Pronghorn Resort

Treat Mom to a special day at Pronghorn Resort! Our beautiful buffet will make her day. Make your reservations early as this brunch tends to sell out. Does Mom love to play golf? Stay for a round of 18 on our Jack Nicklaus Signature Course. Or schedule her a luxurious massage, facial, body or nail treatment in The Spa to follow brunch.

Spring Finale Weekend at Mt. Bachelor

Close out another amazing season at Mt. Bachelor as locals and visitors celebrate one last festive weekend on the mountain. Drink local brews, participate in fun activities, and get in those last turns of the season! We’re lucky to be able to ride and ski through late-May most seasons—get out there and enjoy what’s left!

Pole Pedal Paddle

If you had to choose one Bend race to name as iconic to this town, it would have to be the Pole Pedal Paddle. The PPP includes Alpine and Nordic skiing, cycling, running and kayaking. It is a race as diverse as the landscapes surrounding Bend. From Mt. Bachelor down to the Deschutes River in the Old Mill District, the PPP proves just how much adventure you can find in one day in beautiful Bend, Oregon. There is a division for everyone — even the kids get to join in on the fun in the Mini PPP. You can race as an individual, pair or team. 

Cascade Cycling Classic

The Cascade Cycling Classic shows off Bend’s true bike town colors. This exciting spectator-friendly event is the longest consecutively run elite stage race in the country and attracts many of North America’s top cyclists and teams. The quality of the race courses, the beauty of Central Oregon and the fun atmosphere of the race makes it a favorite.

Happy Girls Run Bend

This might be one of the happiest, most inspiring running experiences ever. How could it not be with a name like Happy Girls? The 5k, 10k and Half Marathon is a Bend tradition for so many women. Join together for camaraderie and smiles along the course, group yoga in the park, and celebration beers at the finish! 

Sisters Stampede

The Sisters Stampede is the largest cross country mountain bike race in Oregon. Many call it one of the best mountain biking experiences of the season, largely because of its natural beauty and rolling singletrack; but also because it’s a ton of fun. There are 26 different categories as well as a kids race. It’s also a great race to attend as a spectator.

Turn your favorite Bend events into a vacation with a stay at Pronghorn Resort! Keep an eye on our Special Offers for incredible packages!