Your Boo just called….it’s date night in the Old Mill District

All you sweethearts, listen up!

Written by Katie Vargas

Love is in the air, and there’s no better place to spread a little extra romance (or self-love) than in the Old Mill District. Grab your honey, your friends, your family, or treat yourself to a well-deserved solo date. However you choose to spend Valentine’s Day, the Old Mill District has you covered with date nights, charming gifts, festive finds and self-care treats guaranteed to leave you feeling the love. Here’s what to expect this Valentine’s Day.

All month long Regal Old Mill ScreenX & IMAX is running it back for a special lineup of romantic classics and cheesy rom-coms. Choose from a list of films like “The Notebook,” “How to Lose a Guy in Ten Days,” or even films like “My Bloody Valentine” playing in 3D! And did I mention… these showings are going for just $7.99 per ticket. You may have already splurged on the ultimate Valentine’s Day gift, but Regal is here to help you find the balance your boo and your wallet will both love. For a full list of Valentine’s Day featured movies and dates, visit Regals’ website HERE.

For a little extra pep in your step, swing by Sisters Coffee Co. and grab one of their Red Velvet Mochas, carefully crafted to give you that warm, cozy sensation that almost mimics the honeymoon phase. Made with a rich, chocolatey sauce blended with vibrant beets for that iconic red velvet hue, this mocha strikes the perfect balance of sweet and earthy flavors, adding just the right pizzazz for a day dedicated to love. Available for a limited time only, so grab a Red Velvet Mocha this February before it’s gone!

Gal with short hair and yellow and cream striped sweater laughing over coffee with blonde hair girl in black top. At Sisters Coffee Co. in the Old Mill District in Bend, Oregon.

Photo: Gwen Shoemaker

Saxon’s Fine Jewelers is turning up the volume for the season of love with a DJ party as part of its title sponsorship of Wine Walk for Bend’s 2026 WinterFest. Join Saxon’s on Friday, Feb. 13, for a live set by DJ Paradox, spinning everything from ’80s classics to today’s hits to be enjoyed by all ages. Adding to the nostalgia, Saxon’s will also showcase an exact replica of the “Back to the Future” DeLorean, a perfect match for throwback tunes and a can’t-miss photo op. And yes, the jewelry will be just as dazzling, with a lineup of heart-shaped pieces and plenty of other sparkly options for every style. Because nothing says “I love you” quite like jewelry.

OrangeTheory Fitness is ready to get your heart rate up this Valentine’s Day, literally. Nothing says self-love like taking care of your body and breaking a sweat. OrangeTheory Bend is hosting a free Couples Class on Saturday, Feb. 14 (yes, you heard that right, FREE!) as well as a free Galentine’s Class on Sunday, Feb. 15, open to all our Central Oregon girly’s. To celebrate a workout well done, cocktails and treats will be served after each class. Call Orangetheory Fitness in Bend today to reserve your spot. Cheers to you, your partner and your willpower.Orangetheory in the Old Mill District in Bend.

For a romantic dinner date, Lady Bird Cultural Society and Anthony’s at the Old Mill District are offering special Valentine’s Day menus designed to set the mood. Lady Bird’s Valentine’s Day-only menu features indulgent items such as caviar cannoli’s, beet and citrus carpaccio and wood-roasted pork chops, along with luxe add-ons to elevate any meal. The experience begins at $95 per guest. Just a short stroll down the river path, Anthony’s will offer its dinner menu all day Saturday and Sunday, Feb. 14–15, highlighting special features like Steak Oscar and lobster fettuccine for a truly decadent date night. Before you’re seated, stop by Anthony’s selfie lounge fully stocked with heart- and balloon-filled backdrops to capture the moment with your favorite person.

Prefer a cozy night in? Create the perfect at-home date with pampering products from Lush and Bath & Body Works. Draw a bath with a velvety bath bomb, light a candle and let the relaxation begin. Finish the night curled up on the couch with a pink or red festive throw blanket from Hello Sunshine, a few chocolate-covered strawberries and a favorite movie.  Cozy pajamas are highly encouraged!

No matter how you choose to celebrate Valentine’s Day, the Old Mill District is here to help you make it memorable. Whether it’s a top-tier date night or a laid-back shopping spree, the day is yours to enjoy. Spread the love and keep an eye out for Cupid. He’s got good aim this year.