Gilmore Girls Experience

Day 1 – Arrival & Cozy Charm

Settle in at Westbrook Inn Bed & Breakfast, famously known for its decorated Victorian rooms and warm, welcoming hospitality, and small-town community—a vibe Lorelai Gilmore herself would adore. Meander through the Westbrook Town Green, enjoying the leafy charm and friendly greetings from innkeepers who make guests feel instantly at home.

Spend the afternoon in nearby Essex, CT, shopping for unique finds in boutiques and bookstores—just like Lorelai and Rory would on their mother-daughter escapades. Treat yourself to ice cream at Scoops and Slices (Westbrook's whimsical answer to Stars Hollow’s sweet spots). Enjoy dinner at local favorites like Cafe Routier or Bill’s Seafood, then take in a Westbrook Town Beach sunset for a perfect Gilmore Girls-style close to the day.

🏡 Stay at Westbrook Inn Bed & Breakfast
🌳 Stroll Westbrook Town Green
🛍️ Shop & wander in Essex, CT (boutiques, antiques, bookstores) 



🍦 Ice Cream at Scoops & Slices (Westbrook's version of Taylor's Olde Fashioned Soda Shoppe)
🍽️ Dinner at Cafe Routier (an Artisan Restaurant) or Bill’s Seafood (for a famous Connecticut Lobster roll)
🌅 Sunset at Westbrook Town Beach

Day 2 – Quirky Adventures & Coffee Fixes

Begin with a delicious breakfast at the inn—much lauded by guests—and fuel up with coffee at Julie’s Cup of Joe, Westbrook’s version of Luke's Diner. Go antiquing in Westbrook and Clinton, channeling the Gilmore spirit of seeking out treasures and quirky knick-knacks.

Lunch at Liv’s Oyster Bar in Old Saybrook means fresh seafood and good company; afterward, stroll through more shops or immerse yourself in Connecticut River heritage at the local museum. For true Gilmore fans, add a Yale University campus visit—Rory Gilmore’s alma mater, which is central to her journey on the show. Dinner options abound: The Essex Restaurant, Penny Lane Pub, or even pizza in your room for a Netflix marathon. Cap the night with live music or a show at The Kate, mirroring the performing arts moments often seen in Stars Hollow.



🥞 Breakfast at Westbrook Inn
☕ Coffee at Julie’s Cup of Joe (Westbrook's version of Marty's Café)
🪑 Antiquing in Westbrook & Clinton
🦪 Lunch at Liv’s Oyster Bar (Old Saybrook)
⚓ Afternoon: browse shops & visit Connecticut River Museum (Essex) or choose to visit the Yale University campus, Rory Gilmore's alma mater.
🍷 Dinner at The Essex Restaurant, Penny Lane Pub, or choose to order in Pizza.
🎶 Evening show or live music at The Kate – Old Saybrook

Day 3 – Beachside Farewell

Soak up nature's peace with a walk at the Stewart B. McKinney Wildlife Refuge, then enjoy brunch at Cristy’s, a Westbrook staple. Cruise through Saybrook Point Marina, then sip your final coffee at Grounds Coffeehouse in Old Saybrook—just right for reflecting on memories, much like Lorelai and Rory’s meaningful moments over coffee.



🚶 Morning walk at Stewart B. McKinney Wildlife Refuge 

🥞 Brunch at Cristy’s (Westbrook) 

⛵ Drive through Saybrook Point Marina 

☕ Farewell coffee at Grounds Coffeehouse (Old Saybrook)

Gilmore Girls History & Extra Magic

The Westbrook Inn is only a short trip from Washington Depot, the small Connecticut town credited as the real-life model for Stars Hollow and beloved by fans as a pilgrimage site. The surrounding area is dotted with spots reminiscent of the show’s scenes and spirit, from tranquil greens to quirky shops and inviting cafés.



Celebrating 25 years of Gilmore Girls, Westbrook Inn proudly offers a Gilmore Girls Package: enjoy themed treats upon arrival, a rundown on the best local pizza joints, and a gift certificate for Scoops and Slices & Julie’s Cup of Joe. It’s the closest you’ll come to living in Lorelai’s and Rory’s world—without leaving Connecticut, and the perfect Gilmore Girls fall road trip.