When it comes to choosing a wedding date, holiday weekends like Labor Day and Memorial Day often seem like a golden opportunity. Built-in vacation time, travel convenience, and the chance to stretch the celebration over several days make these weekends appealing for couples dreaming of an unforgettable wedding experience. But are they really the perfect choice? Oregon vendors weigh in on what couples should consider before committing to a holiday “I do.”
The Perks: Long Weekends = More Time to Celebrate
Many Oregon venues and planners agree: when done right, a holiday weekend wedding can feel like a joyful escape.
“A holiday weekend wedding has a ton of perks, and allows couples and their guests to slow down and truly savor the experience - transforming a single-day celebration into a full, immersive weekend of memory-making,” says Lynne Cahail of Sunriver Resort. “At Sunriver, that could mean time for a custom golf or pickleball tournament, a welcome barbecue, a stargazing party at the nearby Observatory, a wine tasting featuring regional wines, or a moonlight canoe tour down the Deschutes River.” With the added time, couples can turn their nuptials into a full-blown destination event.
Mt. Hood Skibowl is another venue that thrives on holiday weekend weddings, especially over Labor Day. “We love to make a weekend out of it!” shares Shannon Berger-Hammond. “Mt. Hood Skibowl's Adventure Park is the perfect accompaniment to a holiday weekend wedding! With discounts for lodging in Government Camp, we make your wedding weekend an excursion for your guests. From local hiking trails to a dip in Trillium Lake or one of the pools at our resorts - there is fun for everyone!”
Photographer Joie Thongsavath of Simple Joie Photography echoes the appeal. “These weekends are built-in vacation time, which can make travel easier and allow guests extra time to celebrate, relax, and head home without a rush. My advice? If you're planning a holiday weekend wedding, lean into it—offer guests ideas for local excursions, fun activities, or even host additional casual gatherings so it feels like a mini-vacation. That way, it’s a win-win for everyone involved.”
The Pitfalls: Timing Is Everything
While the extra day can be a dream come true, experts also caution that holiday weddings aren’t for every couple or guest list.
“Holiday weekend weddings, like those over Labor Day, can be a double-edged sword,” Thongsavath notes. “As a wedding vendor, I often prefer to reserve holiday weekends for personal time, and many guests may feel the same - especially if they already have annual traditions or travel plans.”
Karlee Patton, a Portland live portrait artist, adds that timing and notice are crucial. “If you're planning your wedding well in advance, securing your date and venue more than a year before the big day, you'll have a good shot at booking your preferred vendors and getting your guests on board,” she says. “But if you're a more spontaneous planner, meaning you won't give guests at least 9 months to make accommodations for a popular weekend, you might be better off steering away from the holiday - unless you're looking for ways to slim down your guest list.”
She also offers a word of caution for out-of-town guests: “One of the biggest benefits of planning your wedding on a holiday weekend is that you give guests who are traveling from out of town some extra time to rest and recover in the midst of travel - but make sure you also give them plenty of time in advance to make accommodations, as hotels and other services get booked up more quickly on holiday weekends!”
Final Takeaway: Make It Intentional
Holiday weekend weddings can offer something truly special if they’re approached thoughtfully. Whether it’s an action-packed itinerary at Mt. Hood or a relaxing retreat at Sunriver Resort, Oregon couples have the opportunity to give guests a one-of-a-kind experience. Just remember: planning ahead, communicating early, and being mindful of guests’ needs will help turn a busy weekend into the best one yet.
Photo Cred: Pacific Northwest Imagery courtesy of Mt. Hood Skibowl
