Gilmore Girls Holiday Getaway

Westbrook Inn Blog

LIVE LIKE A GILMORE GIRL: A HOLIDAY GETAWAY AT WESTBROOK INN BED & BREAKFAST

Ten years ago this November, Netflix brought us back to Stars Hollow with Gilmore Girls: A Year in the Life. It opened with “Winter”: snow around the gazebo, Lorelai in her element, and the kind of small-town holiday magic fans have wanted to step into ever since.

It turns out that feeling exists. It’s in Westbrook, Connecticut.


There’s a town green with a gazebo at its center. There’s a coffee shop run by a real Julie and Joe. There are twinkling lights, familiar faces, hometown traditions, and the sort of crisp winter air that makes you want to wrap up in something cozy and linger a little longer.

This holiday season, Westbrook Inn Bed & Breakfast invites mothers and daughters, best friends, book lovers, coffee devotees, and lifelong Gilmore Girls fans to spend a few days living their own Stars Hollow-inspired story.

Coastline Brewing Company

Your “Live Like a Gilmore Girl” Holiday Package

Some getaways are for checking things off a list. This one is for slowing down, sipping coffee, talking fast, and embracing the cozy little moments.


Add the Live Like a Gilmore Girl Holiday Package to a two-night stay at Westbrook Inn and arrive to a collection of keepsakes and comforts designed for your most charming small-town escape:


  • Two Gilmore Girls-inspired ceramic coffee mugs to take home
  • A copy of Life’s Short, Talk Fast
  • A custom Westbrook Inn book bag
  • A cozy movie-night kit with popcorn and candy
  • Home-cooked breakfast each morning
  • Complimentary late checkout
  • A small-town guide to experiencing Westbrook and the surrounding shoreline like a Gilmore Girl, complete with seasonal festivities, bookstores, cafés, pizza, and boutiques


At $99 per room, per stay, it is the perfect add-on for guests who believe one more chapter and one more cup of coffee are always a good idea.

Surfridge Brewery Bar

Start With Coffee, Books, and a Cozy Inn Stay

A Gilmore Girls-inspired getaway should never feel rushed. Wake up at Westbrook Inn to a home-cooked breakfast, pour something warm into your keepsake mug, and make room for the kind of leisurely morning that usually gets lost in everyday life.


Bring a favorite book, start the one tucked into your package, or settle in for a rewatch with your movie-night kit. With a custom book bag ready for browsing local shops and a late checkout to make departure day a little softer, this is a stay made for taking your time.

Little House Brewery

Find Your Stars Hollow on the Connecticut Shoreline

Westbrook and its neighboring shoreline towns offer the kind of walkable, wonderfully specific local character that makes Stars Hollow feel so beloved. Whether you are visiting for a festive December weekend or simply want a fall or winter escape filled with coffee and small-town charm, there is plenty to build into your itinerary.

Surfridge Brewery Bar

Westbrook Holiday Parade & Tree Lighting

In early December, the town green comes alive with a holiday parade, Santa and Mrs. Claus, ice carving, horse-drawn carriage rides, and the warmth of the whole community gathered together. Add s’mores by the bonfire and a gazebo at the center of it all, and the Stars Hollow comparison becomes pretty easy to understand.


Lorelai would already be outside, looking up at the sky and hoping for snow.

Little House Brewery

Old Saybrook Torchlight Parade

About ten minutes from the inn, the Old Saybrook Torchlight Parade is one of those traditions worth planning a whole weekend around. Held in mid-December, more than twenty fife and drum corps make their way down Main Street by torchlight toward the town green.

The event carries on in any weather and has been a local tradition for decades. It is spirited, historic, delightfully specific, and exactly the sort of community event Taylor Doose would insist everyone attend.a

Surfridge Brewery Bar

Eat Like a Gilmore Girl

No trip inspired by the Gilmores would be complete without great coffee, comfort food, and at least one excellent pizza. Fortunately, the Connecticut shoreline makes that easy.


For a pie worthy of a Friday-night dinner debate, head to Clinton Grand Apizza for New Haven-style pizza. If you are craving a casual shoreline meal with diner-like comfort, Bill’s Seafood is a must-stop and a fitting local answer to Luke’s.


For a more grown-up night out, make a reservation at Charter Oak Tavern, where chef-owner Scott Quinn serves elevated comfort food, including a memorable burger and truffle fries. Then save room for Honeycone Gourmet Ice Cream, a mother-and-daughter-run spot that feels almost too perfect for this itinerary.


In between meals, use your Westbrook Inn small-town guide to seek out local cafés, bookstores, boutiques, and the nearby towns of Essex, Old Saybrook, Guilford, Madison, and Yale. Consider it your own personal Stars Hollow map, just with the Long Island Sound nearby.

Little House Brewery

Bring Your Favorite Person, and Even Paul Anka

This getaway was made for mother-daughter weekends, best-friend reunions, holiday traditions, and anyone who still finds themselves quoting the show around Thanksgiving.



And because no Gilmore Girls-inspired trip should leave a beloved sidekick behind, Westbrook Inn also offers a dog-friendly suite. Paul Anka is welcome, too.

Book Your Cozy Holiday Getaway

Coffee, books, a glowing town green, holiday traditions, and a little extra time together: the magic of Stars Hollow may be fictional, but the feeling is waiting for you in Westbrook.


Book your stay at Westbrook Inn Bed & Breakfast, add the Live Like a Gilmore Girl Holiday Package, and make this season all about small towns, good books, cozy nights, and lasting memories.

BOOK YOUR COZY HOLIDAY GETAWAY