Engagement Season: When and Where to Get Engaged in Upstate NY?

The holidays get the headlines, but another season steals the spotlight each winter: the weeks when romance runs high and “just us” turns into “forever.” Welcome to engagement season.

If you’re looking for the perfect time and place to pop the question, we’re here with simple tips that can turn a beautiful idea into an unforgettable “yes.”

What Is Engagement Season?

Engagement season is different from wedding season. It’s the time of year when proposals tend to surge – with nearly half of all annual proposals happening in the span of a few winter months. It’s that sparkly time of year when we gather with loved ones, celebrate together and reflect on what’s most important. As one year closes and another begins, many couples feel inspired by the idea of new beginnings.

When Is Engagement Season?

You can think of engagement season as bookended by two holidays: Thanksgiving and Valentine’s Day. It’s a time when families come together, traditions take center stage and every moment feels a little bigger. Add in time off work, festive celebrations (and decorations!) and those winter moments made for cuddling, and it’s easy to see why this window feels so romantic and so perfectly timed.

Most Popular Months for Engagements

December consistently stands out as the most popular month for proposals, with Christmas Day as the single most common date to pop the question. The appeal is clear: holiday cheer, time spent with family and a built-in sense of celebration make proposals feel natural.

Other months and holidays shine, too. October has grown in popularity for its cozy vibes, photo-ready foliage and slower, more reflective pace. And if you’re feeling especially grateful for your partner, Thanksgiving can be a heartfelt time to ask. Meanwhile, February – especially Valentine’s Day – remains a classic choice.

Planning Your Wedding Proposal at Turning Stone

Once you’re ready to make engagement season your own, Turning Stone is an unforgettable place to take the next step. The best proposals feel effortless, but they’re built on thoughtful planning. Choose a setting that means something to you and plan a celebration that lets you soak in the “yes.”

Turning Stone makes it easy, with romantic spaces that fit every style. Imagine getting on one knee under the open sky on one of our beautiful golf courses or on the Great Lawn. How about a candlelit dinner at TS Steakhouse with panoramic views? For something more intimate, consider a private room at Wildflowers. And during the holidays, the resort glows with twinkling lights and festive displays perfect for photos and memories you’ll keep forever.

Make Your Special Moment Truly Unique

A memorable proposal isn’t just the question, so plan special moments before and after. A champagne toast over dinner. A spa day for two. Late-night dancing and cocktails. Tickets to a show. Breakfast in bed. A walk through our scenic grounds with a photographer waiting to capture the moment. Turning Stone offers endless ways to craft an engagement that fits your rhythm as a couple – and we’re here to help you make it magical.

Ready to plan the perfect proposal? Contact our team of experts today!

Your Happily Ever After Starts Here

“Yes” is just the beginning, and at Turning Stone it can lead straight into the Big Day you’ve been dreaming of. Explore our venues and wedding packages for everything from intimate ceremonies to grand receptions, all with an expert team ready to handle every detail.

Ready to take the next step? Explore our stunning wedding venues and start planning your perfect day.