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OREGON COAST HEADQUARTERS
2015 NW 39th Street
Lincoln City, OR 97367
CENTRAL OREGON HEADQUARTERS
57100 Beaver Dr Bldg 5, STE 150
 Sunriver, OR 97707
[email protected]
1-541-418-4555
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Your Ultimate May Guide to the Pacific Northwest

May brings longer days, blooming landscapes, and an exciting lineup of festivals and outdoor activities. Whether you’re heading to the Oregon Coast, or Central Oregon, this month offers something memorable for every kind of traveler.

Events in Oregon Coast

Spring Unveiling Arts Festival (May 02-04, 2025)


Location: Cannon Beach, OR
An annual event where galleries unveil new works by featured artists. Attendees can enjoy artist demonstrations, receptions, and a vibrant arts scene throughout the weekend.

Oregon Coast Gravel Epic Bike Race (May 03, 2025)


Location: Waldport, OR
A challenging cycling event that takes riders through the scenic and rugged terrain of the Oregon Coast Range, offering both long and short course options.

Lager Fest at Buoy Beer Co. (May 9–10, 2025)


Location: Astoria, OR
Hosted at Buoy Beer Co.’s new taproom, this festival celebrates lagers with a selection of brews from various breweries, live music, and a festive atmosphere.

Wild Things Festival (May 10, 2025)


Location: Yachats Commons, Yachats, OR
An environmental education event featuring interactive performances, music, and activities focused on nature and wildlife, aiming to inspire stewardship of the natural world.

Ten-Minute Play Festival (May 17, 2025)


Location: Newport Performing Arts Center, Newport, OR
A showcase of original ten-minute plays performed by local talent, offering a diverse range of stories and theatrical experiences in a single evening. ​

Cannon Beach Fat Bike Festival (May 16–18, 2025)


Location: Cannon Beach, Oregon
Three days of coastal adventure with beach rides, guided waterfall tours, a sunset ride at Haystack Rock, a beach party with games, races, and local craft beer sampling.

Florence Rhododendron Festival (May 15–18, 2025)


Location: Florence, OR
Celebrating the blooming of rhododendrons, this festival features parades, a carnival, live music, and the crowning of Queen Rhododendra. It’s a cherished tradition that brings together the community and visitors alike.

Pouring at the Coast (May 31, 2025)


Location: Seaside, OR
A craft beer festival featuring over 30 breweries, live music, and food vendors, providing a lively atmosphere to enjoy the best of Oregon’s brewing scene.

Heroes on the Water (May 31, 2025)


Location: Seaside, Oregon
 An outdoor healing experience for veterans, first responders, and their families. Participants can enjoy kayaking, camaraderie, and the tranquility of nature at Lost Lake.

Events in Central Oregon

Paranormal Cirque II (May 2–5, 2025)


Location: Deschutes County Fairgrounds Expo Center, Redmond, OR
A unique blend of circus, theater, and cabaret with a paranormal theme.

Sunriver Wine & Cuisine Stroll (May 03, 2025)


Location: The Lodge Kitchen, Sunriver, OR
An afternoon of tastings featuring wines from Oregon, paired with creative bites and live music.

Sisters Country Trail Run (May 04, 2025)


Location: Village Green Park, Sisters, OR
Offers 50K and Half Marathon trail races starting and finishing in the heart of Sisters.

Art Meets Wine in the High Desert (May 17, 2025)


Location: SHARC, Sunriver, OR
An all-inclusive event offering tastings from 13 Oregon wineries, accompanied by art, music, and food.

SELCO Pole Pedal Paddle (May 17, 2025)


Location: Bend, OR
A six-leg multi-sport race from Mt. Bachelor to Bend, featuring alpine skiing or snowboarding, Nordic skiing, biking, running, and kayaking.

Bend Women’s Expo (May 24, 2025)


Location: Seventh Mountain Resort, Bend, OR
Features women-owned businesses, interactive breakout sessions, hands-on workshops, and networking opportunities.

Bend Brews & Beyond (May 24-25, 2025)


Location: Drake Park, Bend, OR
Showcasing over 50 Oregon breweries and cideries, including all locally-owned Central Oregon producers, plus non-alcoholic beverage makers.

Kid’s Day in May (May 24, 2025)


Location: The Village at Sunriver, Sunriver, OR
A family-friendly event with games, activities, a petting zoo, bounce houses, and more.

Sisters Stampede (May 25, 2025)


Location: Sisters, OR
A mountain bike race and festival, part of the Oregon XC Series, featuring a 14-mile course.

Things to Do: Coastal Oregon in May

Discover Oregon’s dramatic coastline and encounter fascinating marine life at Cannon Beach, Yaquina Head, and Cape Perpetua.

Beachcombing & Tide Pooling

 Discover Oregon’s dramatic coastline and encounter fascinating marine life at Cannon Beach, Yaquina Head, and Cape Perpetua.

Tour historic lighthouses like Heceta Head and Yaquina Bay to uncover the Oregon Coast’s rich maritime heritage.

Lighthouse Tours

 Tour historic lighthouses like Heceta Head and Yaquina Bay to uncover the Oregon Coast’s rich maritime heritage.

Things to Do: Central Oregon in May

Hike, bike, or paddle through Central Oregon’s scenic trails and lakes — from the Deschutes River to Smith Rock State Park.

Outdoor Recreation

Hike, bike, or paddle through Central Oregon’s scenic trails and lakes — from the Deschutes River to Smith Rock State Park.

Pack a lunch and relax in the sunshine at Shevlin Park or Drake Park, where spring blooms and fresh air await.

Scenic Picnic Spots

Pack a lunch and relax in the sunshine at Shevlin Park or Drake Park, where spring blooms and fresh air await.

Visit local markets in Bend and Redmond for fresh produce, artisan goods, and live entertainment every weekend.

Farmers Markets

Visit local markets in Bend and Redmond for fresh produce, artisan goods, and live entertainment every weekend.

Exploring Olympic National Park

Hike through lush rainforests, alpine meadows, and rugged coastline at Olympic National Park, ideal for outdoor adventure in April and May.

Around the World Embassy Tour

Part of Passport DC in May, this tour grants access to dozens of international embassies for cultural exhibits, performances, and food tastings.

National Gallery Nights: ‘70s Disco Prom

Join the National Gallery’s after-hours experience for dancing, retro fashion, and creative activities all themed around the 1970s art scene.

Book Your May Getaway Today!

May is one of the best times to explore the Pacific Northwest. Fewer crowds, mild weather, and an incredible variety of events make it the perfect month to plan a trip. Whether it’s a cozy cabin near the coast or a family-friendly home in wine country, find your perfect stay with us.

*Prices shown may not be accurate. Please search with dates to view accurate nightly prices

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Search properties
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Average $376 per night includes all fees
$
376
/night (includes fees)
Sep 13 – Sep 15
Manzanita, OR
House
4Bedrooms
3.5Baths
8Guests
Driveway View
Average $236 per night includes all fees
$
236
/night (includes fees)
Sep 29 – Oct 01
Manzanita, OR
House
3Bedrooms
1.5Baths
6Guests
Exterior
Average $488 per night includes all fees
$
488
/night (includes fees)
Sep 07 – Sep 09
Living Area
Average $360 per night includes all fees
$
360
/night (includes fees)
Sep 02 – Sep 04
Sky Island-103
Average $458 per night includes all fees
$
458
/night (includes fees)
Oct 11 – Oct 13
Waldport, OR
Jim's Fancy-139
Average $339 per night includes all fees
$
339
/night (includes fees)
Sep 02 – Sep 04
Anchor Pier View from Patio
Average $175 per night includes all fees
$
175
/night (includes fees)
Sep 13 – Sep 15
Deck View
Average $482 per night includes all fees
$
482
/night (includes fees)
Dec 31 – Jan 02
Lincoln City, OR
living room
Average $265 per night includes all fees
$
265
/night (includes fees)
Sep 15 – Sep 17
Charming coastal retreat nestled among evergreens with mountain and ocean views, offering peaceful privacy near the beach.
Pet Friendly
Cannon Beach, OR
House
3Bedrooms
3.5Baths
8Guests
Pet Friendly
Sunriver, OR
House
3Bedrooms
3.5Baths
10Guests
House
3Bedrooms
2Baths
9Guests
Pet Friendly
Depoe Bay, OR
House
3Bedrooms
2.5Baths
9Guests
Newport, OR
Studio
0Bedroom
1Bath
3Guests
House
3Bedrooms
2Baths
7Guests
Bend, OR
Condo
2Bedrooms
2Baths
6Guests
Patio View
Average $498 per night includes all fees
$
498
/night (includes fees)
Dec 31 – Jan 02
Pet Friendly
Depoe Bay, OR
House
3Bedrooms
3Baths
6Guests
Hot tub
Average $349 per night includes all fees
$
349
/night (includes fees)
Sep 02 – Sep 04
Pet Friendly
Government Camp, OR
Cabin
4Bedrooms
2.5Baths
8Guests
Living Room
Average $176 per night includes all fees
$
176
/night (includes fees)
Sep 02 – Sep 04
Seaside, OR
House
2Bedrooms
1Bath
4Guests
Hot tub
Average $324 per night includes all fees
$
324
/night (includes fees)
Sep 02 – Sep 04
Sunriver, OR
House
3Bedrooms
2Baths
8Guests
Exterior View
Average $304 per night includes all fees
$
304
/night (includes fees)
Sep 06 – Sep 08
Lincoln City, OR
House
3Bedrooms
3Baths
10Guests
Patio Area
Average $313 per night includes all fees
$
313
/night (includes fees)
Sep 02 – Sep 04
Pet Friendly
Depoe Bay, OR
House
3Bedrooms
2.5Baths
8Guests
Outside Front Yard
Average $256 per night includes all fees
$
256
/night (includes fees)
Oct 18 – Oct 20
Manzanita, OR
House
2Bedrooms
2.5Baths
8Guests
A Beautiful Day-111
Average $622 per night includes all fees
$
622
/night (includes fees)
Sep 03 – Sep 05
Pet Friendly
Lincoln City, OR
House
4Bedrooms
3Baths
12Guests
Top Deck Ocean Views
Average $304 per night includes all fees
$
304
/night (includes fees)
Sep 27 – Sep 29
Pet Friendly
Manzanita, OR
House
2Bedrooms
2Baths
4Guests
Fabulous Living Room on the Lower Level
Average $376 per night includes all fees
$
376
/night (includes fees)
Sep 07 – Sep 09
External View of the home
Average $292 per night includes all fees
$
292
/night (includes fees)
Sep 02 – Sep 04
Clubhouse Site 154 (2)
Average $84 per night includes all fees
$
84
/night (includes fees)
Sep 02 – Sep 03
Pet Friendly
Premium Site Y 182 R (1)
Average $98 per night includes all fees
$
98
/night (includes fees)
Sep 21 – Sep 22
Hot Pool Outdoors
Average $412 per night includes all fees
$
412
/night (includes fees)
Sep 02 – Sep 04
The Cozy Pelican-134
Average $270 per night includes all fees
$
270
/night (includes fees)
Sep 10 – Sep 12
Pet Friendly
Lincoln City, OR
House
3Bedrooms
2.5Baths
10Guests
Pet Friendly
Cloverdale, OR
House
4Bedrooms
2Baths
8Guests
Newport, OR
Motorcoach Site
0Bedroom
1Bath
6Guests
Pet Friendly
Newport, OR
Motorcoach Site
0Bedroom
1Bath
6Guests
Pet Friendly
Pacific City, OR
House
3Bedrooms
2.5Baths
8Guests
Lincoln City, OR
House
3Bedrooms
2Baths
8Guests