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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 vary based on dates selected. Please select your desired dates to view accurate nightly prices.

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Living Area
Average $410 per night includes all fees
$
410
/night (includes fees)
Oct 18 – Oct 20
Sunriver, OR
House
4 Bedrooms
4 Baths
10 Guests
Hot tub
Average $145 per night includes all fees
$
145
/night (includes fees)
Oct 18 – Oct 20
Seal Rock, OR
Apartment
1 Bedroom
1 Bath
4 Guests
Top Deck Ocean Views
Average $195 per night includes all fees
$
195
/night (includes fees)
Nov 01 – Nov 03
Manzanita, OR
House
2 Bedrooms
2 Baths
4 Guests
Patio Area
Average $406 per night includes all fees
$
406
/night (includes fees)
Oct 26 – Oct 28
Lincoln City, OR
House
4 Bedrooms
3.5 Baths
13 Guests
Average $344 per night includes all fees
$
344
/night (includes fees)
Oct 18 – Oct 20
Waldport, OR
House
3 Bedrooms
2 Baths
6 Guests
Copy of DSC04548
Average $107 per night includes all fees
$
107
/night (includes fees)
Oct 18 – Oct 20
Bend, OR
Hotel
1 Bedroom
1 Bath
2 Guests
Living Room
Average $498 per night includes all fees
$
498
/night (includes fees)
Oct 18 – Oct 20
Depoe Bay, OR
House
4 Bedrooms
2.5 Baths
10 Guests
Average $114 per night includes all fees
$
114
/night (includes fees)
Dec 31 – Jan 01
Newport, OR
Motorcoach Site
0 Bedrooms
1 Bath
6 Guests
Captain Jack's-110
Average $241 per night includes all fees
$
241
/night (includes fees)
Oct 18 – Oct 20
South Beach, OR
House
3 Bedrooms
3 Baths
6 Guests
Dining Area
Average $177 per night includes all fees
$
177
/night (includes fees)
Oct 18 – Oct 20
Netarts, OR
House
2 Bedrooms
2 Baths
6 Guests
Arbor House
Average $538 per night includes all fees
$
538
/night (includes fees)
Oct 20 – Oct 22
Yachats, OR
House
6 Bedrooms
6 Baths
16 Guests
Outdoor Seating with Beach View
Average $234 per night includes all fees
$
234
/night (includes fees)
Nov 02 – Nov 04
Yachats, OR
House
2 Bedrooms
2 Baths
4 Guests
Average $302 per night includes all fees
$
302
/night (includes fees)
Oct 19 – Oct 21
Sunriver, OR
House
3 Bedrooms
2 Baths
8 Guests
Spacious Living Room with comfortable seating
Average $306 per night includes all fees
$
306
/night (includes fees)
Oct 31 – Nov 02
Pacific City, OR
House
4 Bedrooms
3.5 Baths
8 Guests
View
Average $302 per night includes all fees
$
302
/night (includes fees)
Oct 29 – Oct 31
Neskowin, OR
Townhouse
3 Bedrooms
2 Baths
8 Guests
Average $288 per night includes all fees
$
288
/night (includes fees)
Oct 18 – Oct 20
Bend, OR
House
3 Bedrooms
2 Baths
8 Guests
D & D By the Sea-102
Average $164 per night includes all fees
$
164
/night (includes fees)
Oct 26 – Oct 28
Neskowin, OR
House
2 Bedrooms
2 Baths
4 Guests
Living Room with Comfortable seating
Average $174 per night includes all fees
$
174
/night (includes fees)
Oct 18 – Oct 20
Seaside, OR
House
2 Bedrooms
2 Baths
5 Guests
Oceanfront Deck
Average $302 per night includes all fees
$
302
/night (includes fees)
Oct 24 – Oct 26
Neskowin, OR
Townhouse
3 Bedrooms
2 Baths
7 Guests
Average $197 per night includes all fees
$
197
/night (includes fees)
Oct 20 – Oct 22
Sunriver, OR
House
2 Bedrooms
2 Baths
6 Guests
Hot Tub
Average $329 per night includes all fees
$
329
/night (includes fees)
Oct 19 – Oct 21
Lincoln City, OR
House
5 Bedrooms
3 Baths
12 Guests
Street View
Average $202 per night includes all fees
$
202
/night (includes fees)
Oct 18 – Oct 20
Pacific City, OR
Townhouse
3 Bedrooms
2.5 Baths
6 Guests
Beach View
Average $679 per night includes all fees
$
679
/night (includes fees)
Oct 19 – Oct 21
Lincoln City, OR
House
5 Bedrooms
5 Baths
16 Guests
Hot Tub
Average $317 per night includes all fees
$
317
/night (includes fees)
Oct 18 – Oct 20
Lincoln City, OR
House
4 Bedrooms
3 Baths
12 Guests
Picture yourself grilling up fresh seafood on your private deck, then settling into your choice of sunny seats to savor ocean breezes and a lush coastal horizon stretching toward the water.
A spacious property featuring a pool, manicured lawns, picnic areas, and mature pine trees, set beneath clear blue skies in a tranquil coastal setting.
Modern forest retreat with stunning sunset backdrop and peaceful pine surroundings for the perfect mountain getaway.
Picture yourself dining al fresco as the sky turns shades of pink and blue. Your private patio offers a gas grill for cooking, a spacious table for meals, and cozy seating surrounded by towering pines.
Modern mountain retreat surrounded by towering pines with a striking sunset backdrop. The property's sleek dark siding and warm interior lighting create a welcoming contrast to the natural landscape.