Real Weddings

A North End Boston Wedding with Cigars, Church, and Cannoli

Married at St. Leonard's church, Margaret Jones and Cooper Milano celebrated their love with red florals, family-style Italian fare, and Modern Pastry.

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A bride and groom sitting side by side on a bench inside a church. The bride wears a strapless white wedding dress with floral details and a long veil, holding a bouquet of white and red flowers. The groom wears a dark pinstripe suit with a white shirt and tie, and a boutonniere matching the bride's bouquet. They are smiling and holding hands, with stained glass windows visible in the background.

Photo by Callisto & Co.

August 16, 2025
Assaggio Restaurant & Lounge
Boston, Massachusetts

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For Margaret Jones and Cooper Milano, finding love was a twist of fate during one of the most unlikely times. After moving back home to Massachusetts during COVID, Margaret was unsure how she would meet anyone new until her roommate’s boyfriend unexpectedly connected her to his roommate, who turned out to be Cooper. “It was kind of like a butterfly effect,” the bride says. “Everything just fell into place.” Though the two hit it off immediately, life took them in different directions when Cooper moved to Arizona for work. Still, their connection was undeniable, so he eventually decided to return to Boston—this time for good.

A few years later, that same sense of serendipity carried through to their engagement. During a family getaway in Kennebunkport, Maine, Cooper surprised Margaret with a proposal on the beach outside their favorite spot, the Tides Beach Club, complete with a hidden photographer and both families waiting in the wings with champagne and cowbells. “I thought that I had made all these plans [for the day],” she says, laughing, “when he secretly was planning above my plans.”

A wedding ceremony taking place inside a grand church with ornate architecture. The bride, wearing a white lace gown with a long train, and the groom, in a dark suit, stand facing each other holding hands in front of an altar. A priest in white robes stands behind the altar. To the left, a bridesmaid in a red off-shoulder dress watches, and to the right, two groomsmen in light-colored suits stand side by side. The background features a large, colorful religious mural with angels and saints, framed by tall columns and intricate gold detailing.

Photo by Callisto & Co.

When it came time to wed, the couple decided to honor their relationship’s roots. They ultimately opted for an intimate celebration in their favorite part of the city, the North End, marrying at St. Leonard’s church surrounded by their closest family and friends during Fisherman’s Feast. With rich red florals—nods to the neighborhood’s Italian influence—and a cozy dinner-party vibe, the event embodied what mattered most: family, connection, and the joy of keeping traditions while simultaneously making the experience entirely their own.

A bride and groom stand closely together on a city street, about to kiss. The bride wears a strapless, floral lace wedding gown and holds the train in one hand. The groom is dressed in a dark pinstripe suit with a tie and a boutonniere. Behind them, a building with striped awnings and flower decorations is visible, along with several casually dressed pedestrians crossing the street. The photo is in black and white.

Photo by Callisto & Co.

THE MUSIC

Because the event was held in the North End there were restrictions on amplified music, so the couple had to work around that. “We ended up having a guitar and a violinist who led us from the church to the restaurant, so guests knew where they were going,” the bride explains. “Then they stayed throughout cocktail hour and came upstairs for dinner and a portion of the night.”

THE TRADITIONS

“My ‘something borrowed’ was my older sister and maid of honor’s wedding dress, which I wore for the reception,” Margaret reveals. “We bought it from Unbridaled in Austin, Texas, where she lives. It fit perfectly, and I bought a neck scarf to make it my own. This was a money saver and also so sentimental.” The couple also burned the same candle the bride’s sister used on her wedding day for additional good luck.

Five women stand outdoors on grass with trees and flowers in the background. The woman in the center wears a white strapless wedding gown with floral details and a veil, holding a bouquet of flowers. To her left, one woman wears a red off-the-shoulder dress with ruffles, and another wears a green halter-neck pleated dress. To her right, one woman wears a sleeveless floral dress with a pearl necklace, and another wears a red sleeveless dress with ruffles and metallic sandals. All are smiling and appear joyful.

Photo by Callisto & Co.

THE FIRST LOOK

Before the ceremony, Margaret’s girlfriends came over for a “first look” before her father arrived for his. “They surprised me with a playlist of songs that reminded them of me—I had to guess who picked each one,” the bride says. “It was such a sweet, joy-filled moment that helped calm my nerves and set the tone for the day.” Additionally, as part of her look, Margaret wore feathered Jeffrey Campbell kitten heels she bought on a girls’ trip long before she met Cooper, which were still in the box, never worn, and originally saved just for her “bridal era.”

A street scene at dusk with a traffic jam of cars and pedestrians walking on the sidewalk. On the right side, a large vertical sign for "Assaggio Cucina Positano" features an image of a coastal town with colorful buildings on a hillside. The left side shows a brick building with fire escapes and windows. The atmosphere suggests a busy urban area.

Photo by Callisto & Co.

A dining table set for four with white tablecloth, red napkins, and menus. Each place setting includes a wine glass, water glass, and silverware. The centerpiece features a bouquet of red and white flowers, a tall lit candle in a glass holder, and a table number card with a red apple illustration and the number 2. The background shows a red cushioned bench and a brick wall.

Photo by Callisto & Co.

THE VENUE

For Margaret and Cooper, selecting a venue—one of which was Assaggio—was based on accommodating their guests. “We never dined there before,” the bride admits, “but I loved the other restaurants from DePasquale Ventures, so I knew the food would be good.” After narrowing it down to two places, the couple fell in love with Assaggio’s event coordinator, Mikhael, which sealed the deal. “I got such a good vibe from her, and it was all exactly what we wanted. Plus, Assaggio is attached to the church, so no one had to go far.”

A man and woman are cutting a large, multi-layered cake decorated with piped frosting and topped with strawberries. The man is holding the knife, and the woman, wearing a satin dress with thin straps, is smiling and looking at the cake. Other people are visible in the background, including an older woman clapping. The image is in black and white.

Photo by Callisto & Co.

THE FOOD

The couple wanted people to feel like they were at a feast, passing around different dishes and foods. That included some classic North End Italian fare like raviolis and meatballs, along with some Assaggio special sides, because they thought the experience should be a unique combination of what the restaurant offers. “We tried to make the cocktail hour feel like social bites, which is how dinner ended up being as well,” the bride says. “We wanted it to be like a large grazing table where everyone went around family style and grabbed whatever they wanted.”

Six men dressed in formal attire, including suits, dress shirts, ties, and suspenders, stand closely together against a stone and brick wall. Each man is smoking a cigar, with some holding the cigars near their mouths and others holding them in their hands. The photo is in black and white, and the men appear to be enjoying a social moment.

Photo by Callisto & Co.

THE GOODIES

The couple got cigars for all the guys in attendance because the groom and the bride’s uncles enjoy smoking them. “That was fun to do out in the street,” Margaret says, “and it was a nod to the North End.” Each guest was gifted a takeaway box from Modern Pastry on the way out. “But people were so full at the end of the night that half of the guests left without them,” she laughs. “I couldn’t believe the amount of food that came out. It was like a never-ending feast!”

Stack of white pastry boxes tied with red and white twine, featuring a red illustration of buildings and the text "Modern Pastry" along with contact information. The boxes are arranged on a white surface with a dark background.Photo by Callisto & Co.

THE FIRST DANCE

While the couple didn’t have an official first dance prepared, that was what made theirs so fun. “We talked about doing it and decided not to, but then we ended up having an impromptu spin when one of our friends put on ‘Iris’ by the Goo Goo Dolls and told us we must dance,” Margaret reveals. “It was the end of the night, so whoever was still there at that point—a good amount of people—got to see us.”

Wedding invitations with red bird and floral illustrations, featuring the names Margaret and Cooper, dated 16th of August, 2025, at St. Leonard's Church, North End, Boston, at three o'clock with summer formal attire. The invitations are accompanied by a silver chain necklace, a diamond ring placed on a cluster of yellow cherry tomatoes, and a single red cherry tomato. Silver pins are scattered in the top left corner.

Photo by Callisto & Co.

Two plates each with a grilled steak, sautéed spinach, a bone marrow piece with a spoon inserted, and a creamy white puree, all arranged on white round plates against a dark background. A third plate with bone marrow and puree is partially visible.

Photo by Callisto & Co.

A dining table set with red napkins, white menus, and clear wine and water glasses. In the center, there is a floral arrangement with red and white flowers, including dahlias and hydrangeas, along with some tomatoes. A tall lit candle in a glass holder is on the left side. A table card with a red apple illustration and the number "2" is placed in the middle. The background features a red cushioned bench and a brick wall.

Photo by Callisto & Co.

Bride’s Dress Gabrielle Atelier, Unbridaled (Austin, Texas)
Ceremony Venue St. Leonard of Port Maurice
Flowers Rococo Floral Co.
Groom’s Attire Suit Supply
Hair Abbie Cooke Hair, One Zero Four Salon
Makeup Athra Mikha
Music Joe Sabourin (guitarist), Danielle Turano (violinist), via Music Management
Photographer Cory O’Leary, Callisto & Co.
Planner Jodi Raphael Events
Reception Venue Assaggio Restaurant & Lounge

First published in the print issue of Boston Weddings 2026 with the headline, “Margaret Jones and Cooper Milano.”

A black-and-white photo of a bride and groom kissing in front of a church entrance, surrounded by guests blowing bubbles. The bride wears a strapless wedding gown with a veil, and the groom is in a dark suit. The scene captures a joyful wedding celebration with guests smiling and participating in the bubble-blowing tradition. The text on the image reads "Boston weddings" at the top and "Best of Boston Weddings" at the bottom.

Rachel Puppolo and Joseph Olson. Photograph by 2026 Best of Boston Weddings winner CityLux Studios.

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