Some places are made for falling in love all over again. Sisters, Oregon, is one of them. This little mountain town is an invitation to slow down. To trade the usual distractions for crisp alpine air, lingering breakfasts, and conversations that stretch long into the evening. Here, you’ll find cozy wine bars, luxurious spa treatments, and trails that lead to breathtaking views.
Whether you’re escaping for an anniversary, honeymoon, or just a weekend away, this carefully curated itinerary blends adventure, indulgence, and intimacy.
Day 1: Arrival & Downtown Charm
Your getaway begins the moment you arrive in Sisters, where the scent of pine lingers in the air and the pace of life slows. Choose a stay that fits your style, whether it’s a private cabin at FivePine Lodge, a centrally located cottage at The Scout, or the rustic charm of Left Coast Lodge, with it’s epic views of the Three Sisters Mountains.
Once you’re settled, take a leisurely stroll through downtown Sisters. Hood Avenue Art showcases regional paintings, pottery, and sculpture, while Rescued Living offers a curated selection of beautiful home décor and gifts. For stylish clothing, accessories, and one-of-a-kind gifts, Bedouin is a must-visit.
For your first night, The Open Door sets the perfect scene. This charming wine bar and bistro serves up seasonal, farm-to-table dishes in a warm, art-filled space. Whether you opt for a cozy indoor table or dine alfresco under twinkling lights, the atmosphere is effortlessly intimate.
After dinner, check for live music at The Belfry, a historic venue known for its intimate concerts. If you’d rather unwind at your lodge, grab a bottle of Oregon Pinot Noir to enjoy back at your accommodation.
Day 2: Adventure & Indulgence
Mornings in Sisters call for something warm in your hands and nowhere to be. Sisters Bakery is the go-to for flaky croissants, sugary donuts, and house crafted breads. If you prefer a sit-down breakfast, Angeline’s Bakery & Café offers organic, locally sourced meals with plenty of vegetarian and gluten-free options.
After breakfast, head outside for an adventure. If it’s warm, take a peaceful walk around Suttle Lake, a scenic 3.6-mile loop framed by towering pines. For a bit more of a challenge, Black Butte Trail offers a rewarding 4.1-mile climb with stunning Cascade views—pack a thermos of coffee and take it all in.
In winter, hit the slopes at Hoodoo Ski Area for a playful morning of skiing or snowboarding just 20 minutes from Sisters. If you prefer a quieter experience, rent snowshoes and explore the snowy trails of Ray Benson Sno-Park.
After working up an appetite, grab lunch at Luckey’s Woodsman, a casual but high-quality spot known for next-level burgers and grain bowls with a welcoming small-town vibe.
Nothing says romance like a luxurious couples’ massage. Spend the afternoon unwinding at one of Sisters’ best spas. Shibui Spa at FivePine Lodge is a tranquil retreat offering deep-tissue massages and soaking tubs. Radiant Day Spa specializes in organic facials, massages, and body treatments to melt away any lingering stress.
For your final night, choose between two quintessential Sisters dining experiences. HØST Supper Club at Lake Creek Lodge offers a cozy, cabin-style dinner featuring a seasonal menu inspired by Oregon’s local bounty.
The Lodge Restaurant at Black Butte Ranch, with its sweeping views of snow-capped peaks and rolling meadows, pairs its fireplace-lit ambiance with dishes like wild-caught salmon and Oregon grass-fed steak. End the night outside, wrapped in a blanket by the fire, with nothing but the crisp mountain air and a sky full of stars.
Day 3: A Slow Goodbye
Let your last morning linger a little longer. Grab a latte and a hearty breakfast at The Cottonwood Cafe or Sisters Coffee Company, then take one final stroll through downtown Sisters.