Tips for a Meaningful and Stress-Free Holiday Gathering

Love what you see? Take a peek at the talent behind the story… Design & Styling: Cherry Blossom Events · Photography: Jessica Bedore · Floral Design: Ebb & Flow · Chairs: A la Crate Rentals · Linens: BBJ/La Tavola

Love what you see? Take a peek at the talent behind the story… Design & Styling: Cherry Blossom Events · Photography: Jessica Bedore · Floral Design: Ebb & Flow · Chairs: A la Crate Rentals · Linens: BBJ/La Tavola


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Do you remember when the biggest holiday entertaining stressors were menu planning, creating a crowd-pleasing playlist, and getting all the place card names right? Yeah, me too. Those were the days! The word ‘gathering’ has taken on a whole new meaning this year and we’ve come to appreciate moments together like never before. We’re heading into a season where gathering is all the more magical, but it feels more challenging to achieve a meaningful and stress-free get-together. Thankfully, we’ve got a few friends in the event planning industry to call on. Today, we’re welcoming Andrea and Sarah of Cherry Blossom Events to the blog to share their gems of advice on the topic, paired with an incredibly beautiful outdoor shindig they crafted. Alfresco Thanksgiving, anyone? Get ready to take notes!

Tell us about this stunning shoot! How would you describe the style of this tablescape?

Planning a getaway to Door County, WI with our close family friends was the perfect way to celebrate the change of seasons in Wisconsin. The Eagle Sands Beach Lodge was the ideal setting for a laid back weekend away. To soak in all of the lakeside beauty we planned a special dinner for one of our nights there. Inspired by the neutral tones of fall rather than their bold counterparts, we chose a palette of textural elements in soft grey, beige, pale blue, and copper. The perfectly soft linens from La Tavola accented with mixed fresh and dried floral in speckled ceramic vases from Ebb and Flow Floral set the perfect tone for the design. Layering in ivory plates in an organic shape, copper flatware, and casual glassware finished out the look.

After watching “The Great Outdoors” together on one of our last weekend getaways, we thought having a dinner of lobster tails in the Northwoods was the perfect menu choice and one that made us laugh throughout the dinner. Finishing the meal with individual skillet cookies made the menu a hit with the little ones too! We loved how Jessica Bedore captured this memorable dinner for our families and we cherish the photos of the kids playing and the perfect relaxing time that was had by all.

Can you share your best tips for a stress-free holiday gathering?

What a crazy time this is for everyone, and with the upcoming holiday’s and thinking about ways to entertain we would say our top 3 keys to success during the pandemic have been:

Stay Outside

Think through creative ways to have an outdoor gathering/thanksgiving! Create a beautiful dinner party outside and get creative with ways to keep guests warm. Think patio heaters, a fire table, a bonfire, a simple basket or two scattered around full of blankets that guests can use to keep warm. Pick a favorite fall cocktail that would warm up your guests as well and with the perfect garnish, it can add to the design of your beautiful tablescape!

Make a plan for your menu ahead of time

It’s always great to take care as much food prep as you can ahead of the actual holiday so that you have that much more time on the actual day for other things that may come up. Keep it simple and don’t overdo the menu. If you want to go all out on a fun and intricate side dish you saw and have been wanting to try—maybe keep it simple on the others so you are making an achievable menu. Be sure to consider what items can be prepped in advance so your menu doesn’t force you to be down to the wire with lots of day of tasks. With COVID this year changing the way even small gatherings look, we’ve had fun with prepackaging foods. You can look like you’ve gone the extra mile by thinking through some fun presentation items (consider wedge-shaped boxes for a piece of leftover pie for each guest to take home). It’s all about the presentation!


Think through ways to keep guests entertained in a safe way outside—setting out lawn games for them to enjoy, have a football game on, an easy scavenger hunt for the kids. Having something for guests to do while you are finishing any last details and also providing a fun and safe environment for them to relax will create good vibes for everyone involved. Even the perfect playlist on in the background with a good bonfire going and some “would you rather” cards or your favorite conversational game.

What are three things every intentional gathering should include?

A good theme

We are a sucker for a good theme, even for a casual Friday night in! Take-out pizza around a fire with “Italian Pizzeria” music on Pandora and some red grape juice for the kids and Cabernet for the adults. Sign us up! Whatever your theme is just think of a way to embody it, and during this quarantine time, it can really serve as a fun escape when travel is limited.

Be an engaged host

We try to remind ourselves that our families and friends want to chat with us too. For as much as we are trying to keep the decanters full and the guests happy—it’s important to sit down with our guests and eat with them. Get a chance to connect and catch up with them as well!

One thoughtful detail

Every gathering we try to infuse one thoughtful detail—a family recipe that we’ve displayed in our best dish, a thoughtful place card made by the kids, a favor for the guests to take that’s simple and inexpensive but creates an experience for them. Sometimes the thoughtful detail is even the perfectly garnished cocktail!

As event planners, you must see all sorts of celebrational traditions practiced. Do you have any holiday gathering traditions you recommend that are a bit more modern than breaking the turkey wishbone?

Every Thanksgiving we rewatch the ‘ Friends’ Thanksgiving episodes. Ever since buying the complete set of all seasons in college, there is a note inside the box where we’ve written down every Thanksgiving episode and it’s always a great laugh to start plugging away at those when November hits.

Our kids have always made these candy turkeys from our own childhood that we set at each place setting for Thanksgiving. They’re so simple—a vanilla wafer for the base then a dollop of chocolate frosting, you set a chocolate-covered cherry on it and frost a Keebler Chocolate cookie to the side of the cherry for its feathers, add candy corn on the top as it’s turkey head/beak. Voila! This is something the kids look forward to every year. Finding a fun and simple holiday item you can make or bake with the kids to include on the table spread, definitely lets them feel included. It’s funny how the right display pieces can really make any project shine. A simple white tray with the most perfectly imperfect candy turkeys on it!

Love what you see? Take a peek at the talent behind the story… Design & Styling: Cherry Blossom Events · Photography: Jessica Bedore · Floral Design: Ebb & Flow · Chairs: A la Crate Rentals · Linens: BBJ/La Tavola

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