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06 May 2025
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Cascade Loop Road Trip Itinerary

Overview of the Cascade Loop Road Trip

Embark on an unforgettable journey through the picturesque Cascade Loop, a 440-mile scenic byway that showcases the diverse landscapes of Washington State. Start your adventure in the vibrant city of Seattle, where urban culture meets natural beauty. From there, venture eastward to the charming Bavarian-inspired town of Leavenworth, nestled in the heart of the Cascades, where you can enjoy unique shops and delightful festivals.

Continue your trip to Chelan, a serene paradise by the crystal-clear waters of Lake Chelan, perfect for aquatic activities and wine tasting at local vineyards. Next, explore the quaint town of Winthrop, with its Old West ambiance and myriad outdoor activities to satisfy adventure seekers. As you proceed, immerse yourself in the untouched wilderness of North Cascades National Park, where you can embark upon breathtaking hikes amid rugged mountains and lush green forests.

Round off your travel by heading to Anacortes on Fidalgo Island, the gateway to the stunning San Juan Islands, offering opportunities for whale watching, kayaking, and exploring a historic downtown. Conclude your journey on Whidbey Island, where you can relax and enjoy beachcombing, visiting art galleries, and discovering historical landmarks like Fort Casey. This road trip promises a quintessential Pacific Northwest experience with unforgettable natural beauty and charming locales.


Recommended Activities

  • Seattle offers a vibrant city experience with iconic landmarks like the Space Needle, a thriving arts scene, and the bustling Pike Place Market. It's also the gateway to stunning natural scenery, surrounded by water, mountains, and evergreen forests.
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    Leavenworth

    Leavenworth is a charming Bavarian-style village in the heart of the Washington Cascades, renowned for its annual festivals, beautiful mountain backdrop, and unique shops. It's a great place to experience a taste of Europe without leaving the States.
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  • Chelan is a picturesque town located by the crystal-clear Lake Chelan. It's perfect for outdoor activities such as boating, wine-tasting at its numerous vineyards, or simply relaxing by the water amidst beautiful surroundings.
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  • Winthrop is a charming town known for its Old West theme, offering a unique and immersive experience with wooden boardwalks and western-style buildings. It's also a hub for outdoor activities like hiking, biking, and fishing.
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  • Trip Point Pin5

    North Cascades National Park

    North Cascades National Park is a pristine wilderness area famous for its rugged mountain landscapes, diverse ecosystems, and a vast network of scenic trails. It's a paradise for hiking enthusiasts and nature lovers seeking breathtaking views and solitude.
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  • Anacortes is a coastal town located on Fidalgo Island, known for its vibrant maritime heritage and as the gateway to the San Juan Islands. Visitors can enjoy whale watching, kayaking, and exploring the charming historic downtown area.
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    Whidbey Island

    Whidbey Island offers diverse landscapes, from sandy beaches and rolling hills to lush forests and charming small towns. The island is perfect for a peaceful getaway, with opportunities for hiking, visiting art galleries, tasting local foods, and exploring historical sites like Fort Casey.
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Tasty Picks

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    SkyCity at the Space Needle

    SkyCity at the Space Needle

    A unique dining experience with panoramic views of Seattle from the iconic Space Needle, offering a rotating dining area with exquisite dishes.
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    The Munchen Haus

    4.6
    $$$$

    The Munchen Haus

    Located in Leavenworth, this Bavarian-style beer garden serves delicious sausages and pretzels, perfect for enjoying the town's festive vibe.
    4.6
    $$$$
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    Winthrop's Old Schoolhouse Brewery

    4.3
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    Winthrop's Old Schoolhouse Brewery

    This brewery offers craft beer and pub fare with a scenic riverside location and a rustic atmosphere reflecting Winthrop's Old West charm.
    4.3
    $$$$
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    Anacortes Ferry Terminal Cafe

    4.1

    Anacortes Ferry Terminal Cafe

    A hidden gem serving fresh seafood and classic American dishes, perfect for a quick bite before or after exploring the San Juan Islands.
    4.1
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    Coupeville's Front Street Grill

    4.4
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    Coupeville's Front Street Grill

    Located on Whidbey Island, this quaint waterfront restaurant is known for its fresh mussels and scenic views of Penn Cove.
    4.4
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Stay Recommendations

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    TreeHouse Point, Washington

    4.8

    TreeHouse Point, Washington

    Located near Seattle, this eco-friendly retreat offers unique accommodation in the trees, providing a peaceful escape amidst nature.
    4.8
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    The Posthotel Leavenworth

    The Posthotel Leavenworth

    A luxurious, adult-only spa resort inspired by European wellness hotels, offering a serene environment and stunning mountain views.
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    The Methow Valley Inn

    4.8

    The Methow Valley Inn

    This charming inn in Twisp provides an authentic and rustic experience with beautiful gardens, perfect for exploring the Methow Valley.
    4.8
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    Sun Mountain Lodge

    4.5

    Sun Mountain Lodge

    Nestled in the Methow Valley, this lodge offers breathtaking views, outdoor activities, and a tranquil atmosphere perfect for relaxation.
    4.5
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    Captain Whidbey Inn

    4.3

    Captain Whidbey Inn

    A historic inn located on the shores of Penn Cove on Whidbey Island, offering rustic charm and beautiful waterfront scenery.
    4.3
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Local Events & Happenings

  • Event Icon

    Stone Temple Pilots

    Stone Temple Pilots

    The event will take place at Evergreen State Fair in Monroe.
    Map IconEvergreen State Fair in Monroe (29.51 mi)
    Calendar Icon30 Aug 2025
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    George Lopez

    George Lopez

    The event will take place at Tulalip Amphitheatre in Tulalip.
    Map IconTulalip Amphitheatre in Tulalip (37.79 mi)
    Calendar Icon24 Aug 2025
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  • Event Icon

    Nikki Glaser: Alive And Unwell Tour

    Nikki Glaser: Alive And Unwell Tour

    The event will take place at Angel Of The Winds Arena in Everett.
    Map IconAngel Of The Winds Arena in Everett (39.81 mi)
    Calendar Icon12 Sep 2025
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  • Event Icon

    Warren Zeiders: Relapse, Lies, and Betrayal Tour

    Warren Zeiders: Relapse, Lies, and Betrayal Tour

    The event will take place at Angel Of The Winds Arena in Everett.
    Map IconAngel Of The Winds Arena in Everett (39.81 mi)
    Calendar Icon20 Sep 2025
    Picture for Warren Zeiders: Relapse, Lies, and Betrayal Tour
  • Event Icon

    Cole Swindell: Happy Hour Sad Tour with Priscilla Block

    Cole Swindell: Happy Hour Sad Tour with Priscilla Block

    There is an inherent risk of exposure to COVID-19 in any public place where people are present. COVID-19 is an extremely contagious disease that can lead to severe illness and death. Senior citizens and guests with underlying medical conditions are e...
    Map IconAngel Of The Winds Arena in Everett (39.81 mi)
    Calendar Icon10 Oct 2025
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  • Event Icon

    The World Of Hans Zimmer - A New Dimension

    The World Of Hans Zimmer - A New Dimension

    The event will take place at Angel Of The Winds Arena in Everett.
    Map IconAngel Of The Winds Arena in Everett (39.81 mi)
    Calendar Icon11 Oct 2025
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  • Event Icon

    BERT KREISCHER: PERMISSION TO PARTY

    BERT KREISCHER: PERMISSION TO PARTY

    There is an inherent risk of exposure to COVID-19 in any public place where people are present. COVID-19 is an extremely contagious disease that can lead to severe illness and death. Senior citizens and guests with underlying medical conditions are e...
    Map IconAngel Of The Winds Arena in Everett (39.81 mi)
    Calendar Icon12 Oct 2025
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Music for Your Journey