DiMillo's On the Water

Welcome Party

Cunningham Farm Events

Wedding Day

Lucky Cheetah

Afterparty 

Our Wedding

We met on Hinge in June of 2024 after Brian messaged Charlotte to ask about the black lab in her photos (yes — she’s hers… and yes — this absolutely worked as an opening line).From that very first conversation, everything felt easy. We clicked right away, started planning little adventures together, and quickly realized this was something real.Over the next year, our relationship grew through weekend getaways, exploring new towns, cozy nights in, and happy trips to Stowe. Brian brought his love of hiking and adventure (even if Charlotte still prefers the scenic routes to the steep ones), and Charlotte brought warmth, humor, and the sense of home Brian had been searching for. By January, we knew we were “each other’s person,” and we moved in together to start building a life we both couldn’t wait for.Now, we’re counting down to celebrating with our closest people — thank you for being part of this next chapter with us. 💛

Charlotte + Brian

Our Story

Photos

Wedding Party

What’s the dress code?Our celebration is semi-formal. Think cocktail attire with a polished, elevated touch — suits or jackets for men, jumpsuits or mid-long dresses for women, and anything that feels festive but comfortable. What will the weather be like?Late October in Maine is crisp and beautiful, with temperatures typically ranging from 50s during the day to low 40s (and sometimes upper 30s!) in the evening.Layers are your best friend — wraps, shawls, and jackets are encouraged once the sun goes down. What shoes should I wear?The ceremony and reception include walking on grass, so please plan for:FlatsWedgesBlock heelsComfortable dress shoesStilettos will not be your friend. Is transportation provided to the venue?Yes! Round-trip transportation from downtown Portland to the venue in New Gloucester will be provided on Saturday. More details (pick-up times and locations) will be shared closer to the wedding. Will the wedding be indoors or outdoors?The ceremony will be outdoors (weather permitting), and the reception will take place inside the beautiful barn and tent at Cunningham Farm. Please dress for both indoor comfort and cooler fall air. Are kids welcome?We love your little ones, but this is an adults-only celebration so all guests can relax and enjoy the evening. What’s the parking situation?If you’re driving, there is ample parking on site. If you’re taking the provided transportation from Portland, you won’t need to worry about parking at all. What time should we arrive?Plan to arrive no earlier than 30 minutes before the ceremony to allow time for parking, settling in, and enjoying the scenery.

Q + A

🛫 Which airport should I fly into?You have two main options: 1. Portland International Jetport (PWM) – Closest &amp; EasiestLocated about 10–15 minutes from downtown PortlandSmall, easy to navigate, and very rideshare-friendlyIdeal if you’d like a simple, low-stress arrival 2. Boston Logan International Airport (BOS) – More Flight OptionsLarger airport with more airlines and routesAbout 1 hour 45 minutes–2 hours from Portland by car or bus 🚗 Getting from Boston (Logan) to PortlandIf you fly into Boston, you have two main options to get to Portland: Option 1: Rent a CarPick up a rental at LoganDrive north to Portland (about 1 hour 45 minutes, traffic dependent)A good choice if you plan to explore more of Maine or stay outside downtown Option 2: Concord Coach Lines (Bus)Comfortable, direct bus from Logan Airport to the Portland Transportation CenterEasy pickup from airport terminalsLuggage stored under the bus, Wi-Fi on boardDrops you in Portland where you can easily use rideshare to reach your hotel 🚕 Getting Around PortlandYou do not need a car to enjoy Portland if you’re staying downtown. Rideshare: Uber &amp; Lyft are readily availableMany hotels, restaurants, shops, and the waterfront are within a short ride or walkPortland is very walkable and compact, so it’s easy to explore on foot once you’re in the city but is NOT a good option for getting to/from the wedding. Please plan to use the provided wedding transportation. More info coming soon.

Notes:&nbsp;Room block rates available until September 22, 2026 2-Night Minimum: This hotel requires a 2-night stay minimum. Loyalty Points: Guests cannot use hotel points within the block.

Hyatt Place Portland Downtown-Old Port Square

Block rates available until September 9, 2026 Loyalty Points: Guests cannot use hotel points within the block.

Hilton Garden Inn Portland Downtown Waterfront

While we do not have a formal room block at this hotel, it is a really quaint, New England style hotel and is conveniently located directly across from the Hyatt.

Portland Harbor Hotel

Travel + Accommodations

🌲 Things to Do While You’re HereWhether you're extending your stay in Maine or looking to fill a free afternoon, here are some of our favorite spots and adventures — with options for every taste and budget.PORTLAND, MAINE — Food, Drinks &amp; Experiences

🍽 Great EatsCasual &amp; AffordableDuckfat — Legendary fries, paninis, and milkshakes. A Portland must.Eventide Oyster Co. — The brown butter lobster roll speaks for itself.Gilbert’s Chowder House — Classic New England seafood, right on the water. Mid-Range FavoritesCentral Provisions — Creative small plates with a warm, lively vibe.Fore Street — Wood-fired Maine ingredients; a perfect “welcome to Maine” dinner.Via Vecchia — Upscale Italian with a chic European feel in the Old Port. Splurge-WorthyScales — Elevated seafood on the waterfront.Twelve — New England flavors reimagined; a true culinary experience.The Honey Paw (Chef’s Counter) — Playful, incredible Asian-inspired cuisine. 🍺 Breweries &amp; DrinksBissell Brothers — Trendy, energetic, iconic Portland beer.Allagash Brewing — Beautiful tasting room + brewery tours.Novare Res Bier Café — A tucked-away beer garden loved by locals.Blyth &amp; Burrows — Cocktails in a moody, speakeasy-style setting.

🚶‍♂️ Sightseeing &amp; Experiences Walk Around the Old PortBoutiques, cobblestone streets, charming cafés, and harbor views. Portland Head Light (Cape Elizabeth)A postcard-perfect lighthouse and oceanside walk — absolutely worth the short drive. Casco Bay Ferry RideHop on a ferry to Peaks Island or take a sunset tour for stunning coastal views- dress warm! Eastern PromenadePicnic, walk, or simply relax overlooking the bay. The Soak Spa at Salt Yard (Portland Harbor Hotel) Shopping in Freeport — Home of L.L.Bean and lots of outlets.

Charlotte & Brian

Charlotte & Brian

C&B

Welcome Party

Wedding Day

Afterparty