From the butterflies of a proposal to the quiet ways we say “I love you” years later, relationships are built on moments both big and small. In this story, we follow the life cycle of love—the engagement, the wedding day, and getaways to keep the spark alive long after the honeymoon is over.
Popping the Question
Engagements come in all shapes and sizes. Some are simple and spontaneous,
while others are elaborate and carefully planned.
But at their essence, they all boil down to the same two things: A question and an answer.
In that spirit, we asked a few local couples questions about their big moments—and the photo shoots that celebrated the joy of saying “yes.”
MARY PAT BULFIN & CHRIS THOMAS
The Proposal?
After his initial plan to re-create our first date went sideways due to an illness, Chris proposed on my birthday in December while walking through the beautiful lights at the Winter Wander at Boar’s Head Resort. We stopped to enjoy the lights and warm up near the fire, and then Chris got down on one knee with a beautiful ring inscribed with “Greatest Adventure” written on the inside of the band.
Photo Location Choice?
We spent the last several years of our relationship living in two different states, 400 miles away from each other, and Chris was doing his advanced
training at UVA Health at the time. So, when Sarah suggested the UVA Grounds, we both agreed it would be perfect.
Engagement shoot advice?
An engagement photo session captures the beautiful season of life that marks the time before getting married and provides an intentional pause during wedding planning to reflect and enjoy the moment with the person you love most.
What do these photos mean to you?
We treasure these photos as beautiful moments in our love story. They remind us to be fully present with each other in the big and small moments of life and to continue taking adventures and capturing those moments through photos to continue celebrating each new season.
Photographer (Mary Pat & Chris):
Sarah Cramer Shields
sarahcramershields.com
Cramerphotoweddings
RON BOEHMER & DALTON COX
The Proposal?
We decided that we would do a joint proposal, and that we would both ask the question at the same time. Over the last few years, we’ve spent many weekends hiking Shenandoah National Park and it has been such a big part of our relationship, so we chose to get engaged there. We hiked up to Stony Man early one morning last April—a few days after the fifth anniversary of our first date—and proposed to each other.
Photo location choice?
We chose Mount Fair Vineyard as we wanted to get our guests excited for our wedding there by using the photos in our save-the-dates and on our website. It’s a remarkably beautiful spot at the base of Shenandoah National Park just outside of Charlottesville. Our photographer also suggested taking photos at the Clifton Inn, which was a perfect choice as we celebrated our engagement there.
Favorite part of the shoot?
Since the first few years of our relationship took place in the pandemic, we spent quite a few dates picnicking in parks. Our photographer suggested bringing a blanket and sparkling wine, so we popped a bottle of spumante that we brought back from a vacation to Italy. Jen captured the moment the cork went flying and it was a great end to the session.
What do these photos mean to you?
The engagement photos are so special to us because it’s such a short period of our relationship—it’s a very specific moment in time when we were about to embark on something exciting and the photos capture that moment so well.
Photographer (Ron & Dalton, Molly & Stephen):
Jen Fariello
Jenfariello.com
jenfariello
MOLLY WATSON & STEPHEN SCHULER
The Proposal?
We got engaged at the place that’s most special to us, Snowshoe Mountain in West Virginia. It was a complete surprise, and so incredible with the sunset and mountains in the background.
Photo location choice?
We thought that Stephen’s parents’ house would be perfect because it was a familiar place that we felt comfortable in, could bring our dog to, and with all the beautiful views we could ask for. We wanted to go somewhere local, too, and we knew that Chiles Peach Orchard would have some fun and relaxed places for photos.
Key element for photos?
We knew we wanted our fur-baby, Coach, to be a part of our engagement photos, since he was not going to be at the wedding. We hoped to capture our happiness as a couple, but also the happiness and laughs that Coach brings to us.
Engagement shoot advice?
We are both very camera-shy, but we don’t regret doing these photos for a second! It’s not only a great opportunity to capture more memories but it’s a great time to get to know your photographer, so you are more comfortable when it comes time for the wedding. They also make for a very special guest book!
Getting Married
Ali Rotatori and Josh Rombach first crossed paths during their freshman year at Middlebury College in Vermont, where they lived in the same dorm and remained close friends throughout school. But they didn’t start dating until a few years after graduating. “To which all our friends said, ‘Thank God, finally!” Ali says.
Now living in Charlottesville, Ali and Josh held their wedding and reception last year at Castle Hill Cider in Keswick, Va. Behind the scenes of their storybook wedding, a group of local vendors worked together in a complex dance of multiple moving parts, all choreographed by wedding planners Dickie Morris and Alex Carr of Just a Little Ditty.
“We’re a team of four women who work with clients who are looking to create a magical, amazing day for themselves and their guests,” says Morris, owner of Just a Little Ditty. “Our job is to be their guide. We’re not just logistics coordinators—we are designers, budget keepers, and a little bit therapists.”
For Ali and Josh, the planning process started with defining their top priorities. “It’s really important to align with your partner upfront on what is most important to you,” says Josh. “There are thousands of decisions to be made, but as long as you know which five are most important to you personally, it makes the others less stressful.”
Establishing those priorities results in a wedding where every detail feels like an extension of the couple’s personalities and values. “Every couple has different non-negotiables,” says Carr. “For Ali and Josh, guest experience was number one. Their top priorities of band, decor, and food were all chosen because of how they would impact the guest experience.
Once the vision for the big day is clear, the planners play the role of matchmaker. “We guide them through selecting trustworthy, amazing vendors, which we think is one of the most important things you can do,” says Morris. “Their services are going to color the entire wedding experience.”
In the pages that follow, take a guided tour of what goes into a wedding, including insights from the wedding planners, the vendors, and the bride and groom.
Wedding Planner:
Just a Little Ditty
justalittleditty.com
justalittleditty
Invitations
Invitations are the first chance to set the tone for the wedding. In this case, the overall design blended the couple’s individual styles, prominently featuring sunny colors that are Ali’s favorites while accenting them with Josh’s favorite dark blue color. The invitation included an information booklet about the wedding weekend, featuring a painting of Castle Hill to give a sense of the venue and the wedding’s artistic style.
Another element of the artwork was a nod to a special guest that would a play a big role at Ali and Josh’s wedding: their black lab, Nelly. “Our dog was a part of the party,” says Ali. “The photos with her in them are some of our favorites—whether she was trying to eat my bouquet or just had the biggest smile with her tongue out.”
Artist Abby Armistead created hand-painted artwork for everything from the invitations to wedding decor. “They had a lot of fun with the paper goods,” says Morris. “Abby created artwork that carried through from the invitations to the bar menu. The signature drink menu and the bar itself were painted in the same style as the invitation, creating a cohesive design theme throughout the wedding.”
Stationery:
Abby Armistead Art
abbyarmisteadart.com
abbyarmisteadart
Photography
“Other than your new spouse, the people you spend the most time with on your wedding day are your planner and photographer,” says Carr. “So, you have to make sure you really like the photographer’s style and enjoy spending time with them.”
The couple chose Sarah Cramer Shields, whose people-focused approach was a perfect fit. “Ali and Josh loved Sarah immediately,” says Morris. “Sarah is all about capturing the people and takes amazing photos of everyone’s interactions.”
Photographer:
Sarah Cramer Shields
sarahcramershields.com
Cramerphotoweddings
Venue
Castle Hill Cider provided an ideal location for Ali and Josh’s 250-person wedding. “With a guest count that large, options can be limited unless you’re setting up a tent,” explains Carr. The venue’s outdoor spaces and patio allowed for a seamless flow between the ceremony, cocktail hour, and reception.
The property’s spaciousness and versatility allowed everything to be hosted on-site—including an after-party in the barn’s loft. “It immediately reminded us of Vermont,” says Josh. “The beautiful barn with mountains in the background captured our attention, but the rest of the property—large glass doors overlooking the patio and pond, huge stage for the band, and a picturesque linden grove that made the ceremony feel so intimate—really sealed the deal!”
Castle Hill added one more touch to the wedding. “One of the special aspects of these agricultural venues is that you can incorporate their local products, such as cider,” say Morris. “As guests arrived, they were greeted with trays of sparkling cider. It was the perfect welcome drink—refreshing, light, and tied into the history of the venue.”
Venue:
Castle Hill Cider
castlehillcider
castlehillcider
Ceremony
Another meaningful touch: Josh’s uncle Robert officiated the ceremony. “Having a loved one officiate can make the moment incredibly even more personal and full of warmth,” says Morris. Since Robert wasn’t legally certified to marry them in the state of Virginia, their official legal wedding ceremony was performed at their rehearsal dinner by Dave Norris, the former mayor of Charlottesville. “This way, you can have a friend or someone who hasn’t married anyone before marry you on the day of your wedding.”
Cocktail Hour
“One of the couple’s biggest priorities was making sure that the guest experience was not only seamless, but epic,” says Carr. “They wanted every moment to be welcoming, fun, and full of exciting food and beverage moments.”
Following the ceremony, a cocktail hour on the spacious back lawn and terrace was one of the many ways in which this goal was achieved, with an immersive experience provided by The Catering Outfit. The outdoor bar offered a selection of signature cocktails, including blood orange whiskey sours, caliente margaritas, and paper planes—reflecting Ali and Josh’s favorite flavors and adding another layer of personalization to the event.
An on-site wood grill was another key priority for the couple. “They loved the idea of their guests experiencing the wood grill at cocktail hour, and then enjoying the food prepared on it during dinner,” says Carr.
Food & Drinks:
The Catering Outfit
cateringoutfit.com
thecateringoutfit
Dinner
To create a more intimate atmosphere, dinner was served family style, helping guests feel connected as they shared dishes. “The family-style dinner added warmth,” says Carr. “It was a way to make the large wedding feel communal and inviting, like a big family gathering.”
The tables were intentionally varied, with a mix of long banquet tables and smaller round tables to create an interesting arrangement. “The mix of tables helped break up the space and made the reception feel dynamic,” says Morris. “It also gave guests different experiences—some tables had the energy of a lively, communal meal, while others felt cozier.”
Food & Drinks:
The Catering Outfit
cateringoutfit.com
thecateringoutfit
Cake (& More)
Instead of a large wedding cake, Ali and Josh opted for a small cutting cake to honor the classic wedding tradition. The cake was made by Cake Bloom, whose cakes are baked from scratch using quality, seasonable ingredients.
Instead of serving cake to their guests, they opted instead for their favorite dessert: cookies and ice cream. The Catering Outfit served five flavors of gelato, accompanied by warm chocolate chip cookies made by MarieBette.
Cake:
Cake Bloom
cakebloom.com
cakebloom
Cookies:
MarieBette
mariebette.com
mariebettecafe
Music, Dancing & Afterparty
The wedding featured string music for the ceremony and cocktail hour, followed by a high-energy band that played a mix of classic and contemporary hits during the reception. Before the guests joined the bride and groom on the dance floor, a musical moment delivered one of the evening’s most emotional moments. “Ali’s grandpa, Bob Rotatori—known as “Cleveland Bob” when he’s singing—sang The Way You Look Tonight during dinner,” Josh says. “It was really special to be able to have that moment with many of his kids, grandkids, and great grandkids there.”
The reception transitioned seamlessly into the after-party in Castle Hill’s loft space. To keep the energy flowing without signaling the end, the couple staged a faux departure. “We set up a sparkler send-off before the reception was actually over so they could get those classic departure photos without actually leaving the party,” explains Morris. “Then they headed up to the party in the loft space. It was the best of both worlds—an elegant exit and a late-night celebration.”
Music (Cocktail Hour & Ceremony):
Melodious Strings
melodiousstrings.com
melodiousstringsquartet
Music (Reception):
Nationwide Coverage
nationwidecoveragemusic.com
nationwidecoveragemusic
Videography
In choosing a videographer, Ali and Josh were drawn to Silver Streak Productions’ candid, “behind the scenes” style. “A wedding day goes by in a blur,” says Morris. “There’s so many pieces of the wedding day that you can’t be a part of because you can’t be everywhere at once—a video captures the moments you miss.”
Video:
Silver Streak Media
silverstreakmedia.com
silverstreakweddings
Keeping Romance Alive
In 1969, the Martin Agency introduced what would become one of the world’s most enduring and well-known tourism slogans: Virginia is for Lovers. The campaign’s first ad, which appeared in Bridal Magazine, depicted Virginia as a romantic destination, telling the stories of historical “honeymooners” like George and Martha Washington, and Thomas and Martha Jefferson.
That old slogan still holds true, particularly around the rolling hills and picturesque scenery of Central Virginia. Here are just a few romantic getaways, either in town or an easy drive away.
In the Treetops
Perched 2,700 feet above the Dan River Gorge, the five tree house suites at Primland Resort offer a secluded retreat deep in Virginia’s Blue Ridge Mountains. Crafted from red cedar and designed in France by renowned tree house architectural firm La Cabane Perchée, these elevated hideaways provide sweeping views that stretch from Roaring Creek Gorge to as far away as Pilot Mountain, North Carolina.
Designed to accommodate two adults, each tree house features a king bed, private bath, and spacious deck—perfect for taking in the scenery by day or stargazing at night. Complimentary continental breakfast is delivered to the door each morning and guests can enjoy an included self-guided wine-tasting experience curated by Flowers Vineyards and Winery.
Located in Meadows of Dan, Va., Primland also offers hiking, horseback riding, fly fishing, and an award-winning golf course, along with farm-to-table dining and a luxury spa.
University Oasis
In a neighborhood on the outskirts of University of Virginia, the Oakhurst Inn blends history, hospitality, and modern amenities. Four Craftsman-era residences that were originally built for UVA students and faculty in 1913 served that purpose for nearly a century. Following an extensive renovation of those buildings, the Inn made its debut in 2014 as Charlottesville’s first contemporary boutique hotel. The restoration retained many of the original architectural details while incorporating contemporary design elements.
Mornings begin at the Oakhurst Inn Café, a local favorite serving breakfast, lunch, and weekend brunch. Later in the day, sip a craft cocktail or a glass of Virginia wine at the lobby bar before unwinding in the sauna or enjoying an outdoor fire beside the pool. And even with the University nearby, you’ll still get a peaceful night’s rest—every room comes equipped with a white-noise machine.
Countryside Escape
The Inn at Willow Grove offers an escape into Virginia’s pastoral elegance—without the need for a long journey. Located in Orange, Va., this 40-acre estate blends friendly Southern hospitality with modern luxury in a setting described as “bucolic and serene, comfortable and elegant.”
A restored circa-1778 manor house has been transformed into a Forbes Travel Guide four-star inn with 25 rooms and suites, each luxuriously appointed with plush furnishings, deep soaking tubs, and curated art. The Inn’s Vintage Restaurant and Pub features regional American cuisine with a creative twist, showcasing the freshest locally sourced ingredients.
The on-site, 3,000 square-foot Mill House Spa offers an extensive menu of massage, face and body treatments, and holistic wellness services. And for the ultimate getaway designed for relaxation, romance, and refined dining, consider the Inn’s “Signature Escape” package.
Downtown Decadence
In the heart of historic Charlottesville, The Inn at Court Square offers a stay steeped in elegance and history. This charming boutique hotel spans two meticulously restored buildings. The Butler-Norris House is the oldest existing house in historic downtown, built in 1785 by Edward Butler, a signer of the Albemarle County Declaration of Independence in 1779. It retains much of its 18th-century craftsmanship, including Georgian mantels and dentil moldings. Next door, the Molly Johnson House, built in 1918, showcases rare Mansard roofs, a hallmark of early 20th-century architecture.
Innkeeper Candace DeLoach brings the hospitality of her native Savannah to Central Virginia. The decor is curated by DeLoach and her brother Michael, reflecting their decades-long career in design, with a mix of traditional antiques and mid-century modern pieces. Each of the inn’s ten guest rooms features private baths, with many offering working fireplaces and whirlpool tubs.