Planning your dream wedding weekend: Expert tips and ideas

If you’re dreaming of a celebration that goes beyond a single day, planning your wedding weekend might be the perfect fit. Whether you’re hosting a destination wedding or staying close to home in Oregon, a multi-day wedding experience creates space for deeper connection, more joy, and unforgettable moments with your favorite people.

As an experienced Oregon wedding photographer, I love capturing weekend celebrations from the vineyards of the Willamette Valley to the mountain views of Bend. Here’s my expert advice to help you design a thoughtful and seamless wedding weekend — from welcome dinners to farewell brunches.

Why Choose a Wedding Weekend? | Pacific Northwest Weddings

One-day weddings can feel like a whirlwind. With so many people to see and events to fit in, it’s easy to feel like it all flies by. Hosting a wedding weekend gives you time to slow down, connect with guests, and create a shared experience filled with intention.

Pacific Northwest weddings are especially suited for weekend celebrations thanks to the region’s scenic beauty, outdoor adventure, and cozy accommodations. Whether you’re gathering around a fire pit in Bend or wine tasting in Dundee, your guests will love being part of something bigger than just the ceremony.

Welcome Dinner or Welcome Party | Portland Wedding Photographer Insights

Start your weekend off on the right note with a thoughtfully planned welcome party. Whether you’re keeping things casual or going full glam, this event sets the tone for the rest of your wedding weekend. It’s the first impression your guests will have — and a great opportunity to bring everyone together before the big day.

Tips for Planning a Seamless Welcome Party:

• Choose the right time and location: The evening before the wedding is ideal. Pick a venue that’s easy to access from where most guests are staying, especially if your wedding is at a destination.
• Keep the food easy and fun: Consider local food trucks, grazing tables, or even a pizza and prosecco night. A relaxed vibe makes everyone feel at home.
• Include light entertainment: A live acoustic set, backyard games, or even a welcome toast can add just enough structure without feeling formal.
• Plan for speeches wisely: If you have a lot of toasts planned, this is a great time to do them. That way your wedding timeline stays focused on the ceremony and reception.

Ideas to Make Your Welcome Party Unique:

• Host a themed event: Think coastal clambake, wine tasting in the vines, or retro backyard BBQ — especially fun for Oregon weddings or destination weekends with local flair.
• Custom welcome cocktails: Create a signature drink that ties into your story or your wedding location. Think lavender spritz for wine country or huckleberry mojitos in the mountains.
• Personalize your décor: Use vintage family photos, a chalkboard itinerary, or hand-painted signage to create a sense of connection and storytelling.
• Set up a guestbook alternative: Try a Polaroid station, message-in-a-bottle notes, or postcards from your wedding destination that guests can sign and drop in a box.
• Create lounge zones: Rent cozy outdoor furniture or create a fire pit hangout so guests can relax, mingle, and settle in for the weekend.

As a Portland wedding photographer, I always recommend booking photo coverage for your welcome party. It’s a great time for candid moments, emotional reunions, and sweet interactions all without the tight schedule of your wedding day.

Group Activities to Build Connection

Oregon’s natural beauty offers endless opportunities for outdoor fun: kayaking, hiking, wine tours, or a spa morning. Group activities help guests connect and build anticipation before the ceremony. For destination weddings, these excursions are often a highlight.

For Bend weddings, couples and guests often explore Smith Rock or enjoy a scenic brewery crawl the day before their vows. Consider a group hike at Silver Falls State Park, a private wine tasting in the Willamette Valley, or a relaxing spa day at Allison Inn & Spa. These experiences are perfect for destination weddings and help guests feel immersed in the beauty of Oregon.

Planning a destination wedding outside of Oregon? The same principles apply. Think local flavor, scenery, and shared experiences. In Mexico, consider a catamaran cruise for your guests, a mezcal tasting tour, or a sunset beach bonfire. In Italy, a pasta-making class or vineyard tour through Tuscany creates unforgettable memories. For mountain weddings in Colorado, plan a scenic gondola ride, group hike, or après-ski hangout. Lean into what makes your location special and give guests a taste of it. These moments are often the most talked-about parts of the weekend.

The Main Event: Your Wedding Day

With the groundwork laid, your actual wedding day can be fully enjoyed. Everyone is more relaxed, your timeline is smoother, and the overall vibe is more intimate. For some couples this weekend may be the first time family and friends are meeting eachother. I always tell my couple, “your wedding will likely be the biggest dinner party you’ll ever host.” Whether you’re tying the knot in the forest or at an upscale estate, your weekend foundation makes a big impacton on your guests memories (and yours!) for years to come.

Farewell Brunch

End on a high note with a casual brunch the next morning. Think poolside party! It’s the perfect way to say thank you and goodbye, rave about what a wonderful weekend it was, especially if you’re hosting a destination wedding where guests have traveled far. Bonus: brunch is one last chance for beautiful candid photos.

Looking to make it extra memorable? Consider hosting your brunch at a local vineyard or lodge with scenic views – like Black Walnut Inn in Dundee or FivePine Lodge in Sisters. You could also bring in a local coffee cart or pastry truck for a unique Oregon touch. Add lawn games, soft acoustic music, or a DIY mimosa bar to create a relaxed yet elevated send-off that your guests will remember.

Venue Tips | Oregon Wedding Venues That Shine for Wedding Weekends

Some of my favorite Oregon wedding venues for full weekend celebrations include:

• Black Butte Ranch – Ideal for mountain views and onsite lodging.
• Wind Mountain Ranch – A scenic Columbia River Gorge venue with sweeping views and open-air charm.
• Black Walnut Inn – A romantic escape in wine country.
• Brasada Ranch – A luxury resort in Central Oregon with panoramic views and top-tier amenities.

Look for venues that offer weekend buyouts, onsite accommodations, or flexible spaces for rehearsal dinners and brunches.

How to Elevate the Experience | Destination Weddings Done Right

• Create a printed itinerary or welcome bag with the weekend schedule.
• Hire a planner or coordinator familiar with multi-day events.
• Book your photographer for full-weekend coverage. Including welcome parties and brunch so no moment is missed.