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Spotlight: Pros and Cons of a Holiday Weekend Weddings

Wisconsin wedding pros share their insights on whether or not to hold wedding over a holiday weekend.

July 27, 2025

When it comes to choosing a wedding date, holiday weekends like Labor Day and Memorial Day can be both a blessing and a balancing act. On one hand, there’s the bonus of a built-in three-day weekend - ideal for travel, recovery, and stretching the celebration. On the other hand, you’re also contending with peak travel periods, higher vendor demand, and guests’ pre-existing traditions.

So is a holiday weekend wedding in Wisconsin the perfect fit for your big day? We turned to seasoned local pros to find out.

Yes to the Extra Day - But Plan Ahead

For many, the added day off is a major win for guests and couples alike.

“Holiday weekend weddings? My answer is: YES - with a little caution,” says Caroline Cavalcante, owner of Caroline Cavalcante Photography. “The extra day off gives guests time to travel or recover, the light is dreamy for photos, and there’s a celebratory vibe in the air. If you’re set on a holiday weekend, plan early, communicate clearly with your guests, and be prepared for a bit more coordination.”

Jennifer Janssen of Jennifer Janssen Bridal Artistry agrees: “I always encourage couples to consider holiday weekends like Labor Day. You get a built-in extra day which means more time to celebrate, recover, or travel. It also opens the door for Friday welcome events or Sunday brunches that don’t feel rushed. If you're planning early and love the idea of a full wedding weekend, it can absolutely be worth it. Take advantage of the bonus day. It's a whole vibe.”

“Personally, I’m a fan of holiday weekend weddings, shares Renee Tantillo of Renee Breanne Design + Co. "They offer the perfect opportunity to extend the celebration. With the extra time, you can host a welcome party, a post-wedding brunch, or even plan fun group activities, creating a full weekend experience rather than just a single day. It allows everyone to relax and celebrate without feeling rushed.

Peak Weekend, Peak Planning

The added time comes with a tradeoff as vendors book up fast, and travel isn’t cheap.

“Labor Day weekend is a wonderful time for a wedding; I highly encourage couples to consider it,” shares Maria Bartolotta of The Bartolotta Restaurants. “Most people have three days off in a row, making travel easier. But given it is a holiday weekend, costs can sometimes be a bit higher because staffing can be more challenging. This is why it is important to plan ahead and always work with a budget.”

Mitch of Mitch and Jenna Weddings adds, “The best advantage to booking a wedding over Labor Day or a holiday is the added day of time off for you and your guests. Just remember the downside might be the availability of vendors, venues, and even your guests to attend. Holidays are busy and possibly more expensive.”

It Depends on Your Guest List

Some guests may welcome a wedding weekend; others might have long-standing plans.

“I’m a little biased - my own wedding was on the Sunday of Labor Day weekend,” says Bobbi Petersen of Bobbi Petersen Photography. “Between my personal experience and years of photographing weddings over the holiday, I’ve learned there are no absolutes. One couple might expect half of their guest list to attend and end up with a 95% turnout. Another might be surprised at how many guests already had travel or family plans locked in. It really depends on your people and their holiday routines.”

Her advice? “Send save the dates as early as possible. Giving your guests time to plan or rearrange existing plans can make all the difference in your turnout!”

Wisconsin’s Weather Advantage

If you’re eyeing an outdoor ceremony, Labor Day weekend could be ideal.

“September in Wisconsin is nothing short of magical - crisp air, golden sunsets, and nature putting on its best show,” says Drew Hawley of Flowers for Dreams. “For floral designers, it’s a dream. Local flower farms are overflowing with peak-season varieties, offering an incredible selection of fresh, vibrant flowers to design with.”

That said, the long weekend rush can put a strain on vendors. “Labor Day can be tricky on the staffing front. By September, many of our reliable summer hands are back in school or unavailable. That means pulling off a big wedding design requires extra planning and resourcefulness,” Drew adds.

Glam Time & Guest Experience

Holiday weddings can also mean a more relaxed pace on the big day.

According to Beauty Unveiled by Tia, “With fewer people rushing off to work on Monday, the wedding day schedule can feel less crunched, giving more time for touch-ups, portraits, or relaxed prep. Early September often delivers beautiful late-summer light without the peak heat of July/August. Outdoor ceremonies and glam photoshoots? Yes, please.”

Still, it’s important to think about your guests’ traditions. Cass Stone of C.Mae Photography advises, “While sharing your wedding anniversary with a major holiday can be meaningful and festive, it’s important to remember that many families have long-standing traditions during these times. If you’re considering a holiday weekend wedding, think about planning it a day or two before or after the actual holiday to give guests space to honor their own traditions.”

Bonus: Honeymoon Hack

If you’re jetting off after the wedding, Labor Day weekend can help stretch the magic.

“A honeymoon over Labor Day weekend is a brilliant idea,” says Tayna Lippincott of Bradford Street Travel. “The standout advantage is you won’t need to use PTO for the holiday itself, and since many people are already out of office before and after, it's the perfect time to stretch your honeymoon. With a little strategy, you can plan your trip so the holiday falls in the middle, helping you avoid peak airport crowds and score better pricing on flights (especially if you book early). Plus, if you opt for a non-traditional destination - or one that doesn’t celebrate the same holiday - you might find more availability and even lower rates. Working with a travel advisor can make all the difference when it comes to avoiding common pitfalls, matching you with the perfect destination, and turning your Labor Day weekend honeymoon into something effortless and elevated.

Final Takeaway: Know Your Crowd, Start Early, and Celebrate Big

As David Porto of Blue Plate Catering puts it: “We encourage holiday weekend weddings. It's a great opportunity for a built-in three-day weekend, allowing for out-of-town guests to have a bit more breathing room with respect to travel plans. It's especially helpful if you have multiple activities planned on different days.”

Holiday weekends can bring joy, flexibility, and unforgettable moments - as long as you’re prepared. From early save the dates to budget planning and vendor booking, a little foresight goes a long way. If you love the idea of a weekend-long celebration filled with Wisconsin’s natural beauty, cozy gatherings, and festive energy, Labor Day or Memorial Day could be the perfect time to say “I do.”

Photo by Caroline Cavalcante Photography