The Most Dreamy and Romantic Autumn Weddings

By Cathleen Freedman

When you start wearing your cable-knit sweaters à la When Harry Met Sally and watch the leaves cascade to the ground, you know the most romantic time of the year is near. From the brisk air to the gold and crimson-colored trees, the autumn season is inherently awe-inspiring. Couples are naturally drawn to the idea of marrying under velvet skies and dancing to Neil Young’s “Harvest Moon” at their reception. We’ve compiled a few of our favorite autumn “I dos” on OTM, so if you haven’t already, prepare to fall in love with fall weddings.

Photo: Rachel Buckley

Lucy Drummond and Derrick Brown’s Manhattan-Meets-Vermont Wedding

On a sunny day on the Reading Farms Estate near Woodbury, Vermont, guests walked along the shady tree-lined path of Maple Alley while a harpist strummed. “Being mid-October, the foliage was comprised of auburns, deep greens, oranges, and yellows,” the bride shares. “It was spectacular!” When the mid-day chill sunk in, Lucy’s sister, Vogue alum Selby Drummond, brought her an ostrich feather Morgane Le Fay bolero to wear down the aisle. Later that evening, everyone kept warm with Maple Manhattan cocktails.

Sarah Flint and Sean Beresini’s Intimate Massachusetts Micro-Wedding

Luxury shoe designer Sarah Flint accounted for the chilly fall weather and customized her Reem Acra ball gown with a coat. “I love 19th-century fashion, so I designed a shorter coat that would give the illusion of a bustle and kept it open at the front to showcase the gown’s pleating,” she says. From the sycamore tree and wildflowers at the altar to the reception’s dinner menu and eucalyptus-topped wedding cake, seasonal touches were incorporated the entire day.

Photo: Amarachi Ikeji

Morgan Booker and Philip Gertner’s Refined Wedding in New Jersey

Inspired by the French countryside with a modern twist, this October wedding subverted typical autumnal color palettes. The bride carried a bouquet of delphinium, snapdragon, ranunculus, and roses in an array of whites and blues. The groom opted for a pair of black tuxedo pants from Ted Baker paired with a dark blue velvet smoking blazer from Bonobos.

Photo: Calen Rose

Louise Piyarat Lai and Hoe Jung’s Intimate Wedding in New York

On November 5, 2022, Louise and Hoe had a traditional Korean pyebaek at home with their family. Once officially wed, they joined their guests at Eleven Madison Park for a private five-course meal surrounded by florals by Designs by Ahn. The couple then had an impromptu first dance to their favorite song, “Can’t Help Falling in Love” by Hailey Reinhart, while their family serenaded them. The party continued on a rooftop with an eye-level view of the Empire State Building.

Photo: Perry Vaile

Eddie Irions and Ryan Albert’s Classic Wedding

For Eddie and Ryan, it was an easy decision to start planning for an October 2021 wedding in South Carolina. “We wanted our aesthetic to be classic, elegant, and to capture the natural beauty of the Lowcountry landscape,” Ryan explains. After the last song of the night was played, the new mister and mister excitedly exited through a sparkler tunnel and off into newly married life.

Photo: Davy Whitener Photography

Hannah Stefanek and Cameron Reehl’s Feminine Fall Wedding in Alabama

When Hannah and Cameron could not secure their original reception venues, Hannah called Cameron’s former baseball coach and asked if they could use his alma mater for their wedding. Just like the the throwback venue, the rest of the day’s aesthetic was similarly very 90s-esque. Cameron’s mother suggested Hannah go to New Orleans to search for fabrics and place orders for yards of a vintage silk velvet burnout and a vintage Chanel remnant that would make her unique rehearsal and grand exit dresses. The reception was a fall night to remember. Cameron’s uncle, country singer-songwriter Walker Hayes, sang his single “Fancy Like” and television was wheeled in to show the tail end of the Alabama football game.

Candáce Gregory and James Fils-Aime’s Elegant Brooklyn Wedding

Candáce entertained the idea of hosting her wedding on the lawns of Prospect Park and ended up getting to have the ceremony in the peristyle instead, which ultimately worked out even better for the October nuptials. “We liked the classic architecture juxtaposed with the open natural space of the park centered in Brooklyn, so there was a kind of marriage of natural beauty and refined structure,” the bride explains. The wedding party wore jewel tones, befitting of the autumnal season.

Proud Limpongpan and Jon Biagiotti’s Dreamy Wedding in Huntington, New York

Proud and Jon’s autumn wedding was nothing short of a fairytale. A hundred guests witnessed the exchanging of their vows at the stately Oheka Castle. Their marriage had been graced with blessings from both the Princess of Thailand and Pope Francis. During the feast later that evening, an eight-piece live band serenaded the dining hall and played Tchaikovsky’s “Sleeping Beauty” for the newlyweds’ first dance. Simply enchanting!

Photo: Chaz Cruz

Kelsey Smotzer and Emily Nahas’s Thoroughly New York Nuptials

New York was practically a featured guest at Kelsey and Emily’s autumn wedding. Emily discovered their ceremony violinist Susan Keser at the Union Square subway station four days prior to the wedding. After saying “I do,” the newlyweds and their families  went to Carbone for a wedding lunch of Michelin-star Italian food and wines. That evening, the festivities continued with a cocktail party at Gilligan’s at the Soho Grand Hotel. Then, both brides changed into two very different black minidresses. “We were in downtown Manhattan, after all!” Emily exclaims. The after-party kicked off at The Django jazz club at The Roxy Hotel with a smaller group. Kelsey affirms, “It was the perfect NYC day and night.”

Photo: Ashley Sawtelle

Margaret Carvey and Stephen Hallenbeck’s Ranch Wedding

Margaret Carvey and Stephen Hallenbeck hosted a western-inspired wedding weekend in Wyoming. “I had a real vision for what I wanted for my looks throughout the weekend, and stylist Anny Choi of Over The Moon helped make it happen,” the bride says of her wedding wardrobe. While she originally saw herself wearing a non-traditional color for her wedding day, Margaret changed her mind two months before the big day. Anny swooped in with the ultimate solution, Brock Collection’s brand new Chantilly lace gown.