Fall in Love: Kitsap Couple Escape

Planning a cozy October getaway for two? This 3-day itinerary highlights the best of the Kitsap Peninsula in the fall—think crisp air, scenic strolls, waterfront dining, autumn colors, and charming small towns perfect for slowing down and savoring the season together. 

Day 1: Welcome & Evening Vibes

2:00 PM – 4:00 PM: Arrival and Check-In

• Arrive in the Kitsap Peninsula from the surrounding areas.

• Check into your hotel by 4 PM at Port Gamble Guest Houses this fall to soak in the charm of 19th-century architecture, vibrant community spirit, and the rich autumn colors that make this Olympic Peninsula gem truly magical. Or here are some other options to stay.

Photo by Emma Avery

5:30 PM: Dinner at House 11 Taproom

• Grab a seat at House 11 Taproom in Port Gamble, where you can sip international wines and local brews while enjoying a cozy, laid-back atmosphere and a delicious menu made with fresh, local ingredients. 

Day 2: Ready, Set, Explore!

8:00 AM: Breakfast at Cafe Cocina

• Start your morning at Caffe Cocina with a fresh-brewed coffee in hand and a hearty breakfast sandwich or burrito to kick off the day right.

• Alternative Spots: Butcher & the Baker, Greenlight Dinner, Crabtree or all in the Poulsbo area. 

10:00 AM: Hiking in Illahee Preserve

• Head to Illahee Preserve for a peaceful fall hike, where you can breathe in the crisp autumn air and enjoy a little leaf-peeping among the vibrant seasonal colors.

• Alternative: If you’re looking for a fun Pumpkin Patch you could also check out Pheasant Fields Farm to enjoy some fall festivities. 

12:30 PM: Lunch at McCloud’s Grill House

• Head over to McCloud’s Grill House for delicious eats, a huge menu full of crowd-pleasers, and outdoor seating complete with yard games for a fun, laid-back dining experience.

• Alternatives: Noah’s Ark Restaurant, Taqueros Taste of Mexico, Hop & Drops, and GOGIRO | Korean BBQ & Shabu Shabu Hotpot

Afternoon Activity: Rest and Explore Fall Activities depending on the weekend

• Some nearby attractions:

• Winney Farms for a Pumpkin Patch & Corn Maze

• Port Orchard Fall Farmer’s Market

• Bainbridge Gardens Pumpkin Walk

• Fat Turnip Farms for a Pumpkin Patch & Corn Maze

6:30 PM: Dinner at the Hound & Bottle

• Grab dinner at Hound & Bottle, a cozy neighborhood spot that celebrates the heart of the Northwest with seasonally inspired dishes, classic favorites, and a rotating menu that highlights the best local flavors.

• Alternatives – Depending on your afternoon adventure location

• Axe & Arrow Gastropub – Bremerton

• Bruciato – Bainbridge Island

• Sourdough Willy’s Pizza – Kingston

• Whiskey Gulch – Port Orchard

• Bushel & Barrel Cider House – Poulsbo

Photo by Emma Avery

Day 3: Breakfast, Stroll & Hit the Road: One Last Morning in Kitsap!

8:00 AM: Breakfast at Madison Diner

• Grab breakfast at Madison Diner, a charming 1948 railcar serving up locally sourced, home-cooked meals that stay true to classic American diner favorites.

9:30 AM: Morning Stroll at Fort Ward Park

• Go explore Fort Ward Park, a scenic 137-acre marine park along Rich Passage with 4,300 feet of saltwater shoreline. Once a historic military site, the park now offers a peaceful day-use experience with forested trails, a rocky beach, a boat ramp, and even an underwater park for scuba diving.

• Optional Stop at Pia the Peacekeeper one of the famous Thomas Dambo Trolls

12:30 PM: Lunch Before Heading Home at Sully’s Bistro & Bar

• Sully’s Bistro & Bar is a local favorite for great food, drinks, and Puget Sound views—on a clear day, you can even spot Mt. Rainier!