Port Townsend and the surrounding areas of the Olympic Peninsula are no doubt a tourist hot spot throughout the summer season for outdoor enthusiasts, nature lovers, and those who value art, cultural experiences and expansive views of the water. Locals, however, would agree that winter is one of the best times to visit. For some, the perfect cold-weather getaway involves rest by a cozy fire in a cabin overlooking Discovery Bay. For others, an exhilarating outdoor hike during a morning fog paired with cider tasting in the afternoon while listening to live music brings an energizing reprieve from the rainy season of the Pacific Northwest. If you’re looking for the perfect winter vacation, including dog-friendly trips to the Olympic Peninsula, look no further than these offerings along the gateway to Port Townsend.

Upon the arrival of your stay at Chevy Chase Beach Cabins, furry friends receive these heart-shaped treats made with love from the nonprofit organization Gatheringplace. Photo credit: Jess Caldwell

Where To Stay in Port Townsend For Cliffside Views of the Olympic Peninsula

Chevy Chase Beach Cabins is an exceptional stay that offers all the amenities to provide a restful and cozy vacation. Each cabin is a unique design, with many featuring fireplaces, king-sized beds, full kitchens and expansive views overlooking Discovery Bay.

The owners take great care to make sure every new guest feels as if they are the first to stay there. “We want people to feel comfortable the moment they arrive,” shares Jenn Dickey. Jenn and her husband, Jeff Betinol, who have been the owners since 2012, have kept the spirit of stewardship for this historic location, which has been hosting guest and their pups since 1897.

Jenn and Jeff have a wonderful story on their about page that has all the feelings of a love story. “The beds have down comforters and pillows – we have non-down options too,” shares Jenn. “We take pride in providing clean, well-appointed cabins, and our hope is guests will have everything they need to enjoy their stay.”

These Port Townsend vacation rentals are dog-friendly, too! “We partner with a local nonprofit, Gatheringplace, who makes our doggie treats so that even the pets feel special and welcomed,” adds Jenn.

Chevy Chase Beach Cabins offers the perfect getaway for winter storm watching and a convenient location in Port Townsend that is close to local dining and activities. With private beach access for guests and their dogs,

Where To Eat in Port Townsend: Locally-Sourced and Inspired Dining

Port Townsend has a local gem that is not to be missed while visiting the Olympic Peninsula. Owned by Scott Ross and chef Deborah Talyor, Finistére has brought the energy of Manhattan fine dining to this quaint Maritime town and the menu is exquisitely curated. The locally-inspired menu brings the connectivity of the farming community to the dining experience.

Jason Marsteiner enjoys fine dining with the ease of a casual atmosphere at Finistére in Port Townsend. The oysters are sourced locally, and the sourdough bread is made in-house. Photo credit: Jess Caldwell

Alexander Moats from Chicago, a server who has been with the restaurant for nearly three years, is extremely knowledgeable about the menu and can perfectly pair a wine recommendation with the flavor and texture of the meal. Moats’ favorite dish is the Tagliatelle. “It’s a house-made pasta, Bolognese ragu, that is rich, creamy, and comforting on a rainy winter evening,” he says.

Farm-crafted Cider on Tap and Live Music in Chimacum

Winter weekends offer live music at Chimacum’s welcoming Finnriver Farm & Cidery. Check out their Music & Events Calendar, as they have been voted “Best Live Music Venue” and “Best Dance Venue” in the Olympic Peninsula. For farm-crafted cider on tap, order a flight and head to the heated outdoor pavilion that overlooks the organic orchard.

two people sit at a table in Finnriver Farm and Cidery. One holding a plate of food and the other a drink.
Finnriver Farm and Cidery is a must-experience destination while visiting the Olympic Peninsula. Enjoy a midday farm-crafted cider or kombucha on tap, and make sure to order the buckwheat chocolate chip cookies made from the local flour grown and milled from Chimacum Grainery. Photo credit: Laura Predergast

Plan ahead and schedule time for a tour and tasting. A visit to this special place elicits all the good feels of farm life with a beautiful and intentional aesthetic. Dogs are welcome in the “Bark Yard,” so order lunch from their kitchen or bring a picnic from across the road at the Chimacum Corner Farmstand.

Dog-Friendly Outdoor Activities in Port Townsend During the Winter

Just minutes away from Finnriver Farm & Cidery is HJ Carroll Park. Meander through the Kul Kah Han Native Plant Garden to learn about Pacific Northwest native plants, or wind your way through the Chimacum Creek Labyrinth made from stones to promote a walking meditation.

While in Chimacum, visit the HJ Carroll Park to stretch your legs and walk the dogs. Meander through the Kul Kah Han Native Plant Garden to learn about Pacific Northwest native plants. Photo credit: Jess Caldwell

Put the dogs on a leash and walk the Rick Tollefson Memorial Trail, which offers interpretive signs along the way. This trail winds along the edges of SpringRain Farm. After time well spent at the park, SpringRain Farm offers a farm stand for the public. Stop by and pick up some fresh produce or some of their specialty foods like organic arugula pesto or hand-crafted marinara sauce made from their harvest.

Along with beach walking and hiking throughout the winter, year-round golfing is available at Discovery Bay Golf Club. Take in the Olympic and Cascade mountains while enjoying 18 holes of golf. Located right across from Chevy Chase Beach Cabins, feel free to bring your dog along for the fun as Discovery Bay Golf Club was rated the “#1 “Dog-Friendly Golf Course in the Nation” by Bringfido.com. Opened in 1925, Discovery Bay Golf Club, formerly a part of Chevy Chase Inn, has the distinction of being the oldest public golf course in Washington.

To learn more about planning your next dog-friendly vacation in the Olympic Peninsula, visit the Enjoy Olympic Peninsula website.

Say hello to the farm dogs who protect the pastured ducks and geese of SpringRain Farm while walking The Rick Tollefson Memorial Trail, which can be accessed from the HJ Carroll Park. Photo credit: Jess Caldwell


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