By The Gypsy Nurse

November 8, 2025

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Travel Like a Gilmore: Small Towns That Feel Like Stars Hollow

If you’ve ever wished you could grab a cup of coffee at Luke’s, stroll through the gazebo-filled town square, or catch a quirky community festival, you are not alone. Gilmore Girls made us fall in love with the charm of Stars Hollow.

For healthcare travelers, the good news is you don’t have to rewatch the series to experience that cozy small-town feel. You can find it in real-life Stars Hollow small towns across the country. Whether you’re on assignment or planning a weekend getaway, these small towns bring Star Hollow magic to life.

Stars Hollow Small Towns to Explore:

1. Woodstock, Vermont

  • Known for its charming downtown, covered bridges, and historic inns.
  • Local coffee shops and general stores make it feel straight out of Gilmore Girls.
  • The fall foliage here is especially dreamy! Perfect for Stars Hollow-style fall walks.

2. Mystic, Connecticut

  • Quaint New England vibes, complete with a drawbridge and riverside shops.
  • Coffeehouses and bookstores line the streets, perfect for Rory-style reading afternoons.
  • Community events and farmers’ markets give it that small-town closeness.

3. Leavenworth, Washington

  • A Bavarian-inspired village tucked in the Cascades, Leavenworth is a quirky and colorful town, full of personality.
  • Festivals throughout the year (Hello Oktoberfest!) mirror Star Hollow’s love of quirky celebrations.
  • Cozy cafes and family-owned restaurants make it feel neighborly.

4. Galena, Illinois

  • Cobblestone streets, 19th century buildings, and a charming town square.
  • A hub for antique shopping, local art, and boutique coffee shops.
  • Known for its warm, welcoming community, just like Stars Hollow.

5. Beaufort, North Carolina

  • Coast charm mixed with historic character.
  • Waterfront cafes, bookstores, and scenic strolls echo the slower pace of Stars Hollow.
  • Friendly locals and small-town hospitality make travelers feel right at home.

6. Middleburg, Virginia

  • A picturesque village with rolling hills and horse drawn charm.
  • Independent shops, cafes, and wine spots to explore on your days off.
  • The kind of place where everyone really does know your name.

🚙 Traveling Tips

Healthcare assignments can be fast-paced, but taking time to visit and explore small towns is the perfect way to recharge and unwind after long shifts. Whether you’re sipping coffee in a cozy cafe, wandering through a local bookstore, or enjoying a quirky community festival, you will feel like you’ve stepped into your own Stars Hollow moment.

The Gilmore Girls taught us that home is more about connections and community than a specific place. As a traveler, you can find your very own Stars Hollow in unexpected places of the country. One small town at a time.

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