The Homestead

10/25/2026

We take some things very seriously around here.
🏆Being recognized for our hospitality? Absolutely.
☕Ray's cappuccinos? A matter of considerable importance.
🛌A comfortable place to land? Non-negotiable.
🏠Making you feel at home? Certainly. Even if that means staying in your pajamas till noon. That's ok with us. Your to-do list can wait.

Come see what all the fuss is about. You deserve an award-winning getaway, right here at The Homestead.

10/21/2026

💭If you’re dreaming of a little Gilmore Girls-like New England escape, The Homestead in Madison might be your Stars Hollow by the sea. 🌊

If you could spend a day in Stars Hollow, which Gilmore Girls character would you be?
☕Lorelai Gilmore — Your day doesn’t start until you’ve found your coffee. (Bonus points for a cappuccino!) Your Madison match: Willoughby’s Coffee & Tea or Camper Coffee
📚Rory Gilmore — You’re happiest with a good book, a quiet corner, and absolutely no one asking you to hurry up! Your Madison match: Spend an afternoon browsing R.J. Julia Booksellers.
🍕Sookie St. James — You plan every adventure around your next meal. Your Madison match: Local favorites include Café Allegre, The Wharf, Bar Bouchee, and Grand Apizza!
🥾Luke Danes — You prefer fresh air, a good walk, practical shoes, and keeping things simple. Your Madison match: Take a walk along Hammonasset Beach.
🗓Paris Geller — Your itinerary is meticulously planned. You’ve researched every stop, booked reservations, and timed each trip. Your Madison match: Build the perfect day around the town green, local shops, the beach, and dinner.
🎸Lane Kim — You’re always on the lookout for live music and hidden local gems. Your Madison match: Hear a live musician at Donahue’s Madison Beach Grille or catch a concert on the Madison Green.
🛍Kirk Gleason — You embrace the unexpected, champion local businesses, and turn simple errands into daylong adventures. Your Madison match: Browse downtown shops, explore the green, and let the afternoon unfold.

Now it’s your turn! Which character are you, and what’s the one place in or around Madison you’d have to visit?

Comment and tell us your character — and tag your Gilmore Girls bestie!

10/16/2026

There’s still plenty of time to plan your trip here to see the show!🍁🍂🎃🍎

Here comes another glorious fall weekend! 🍁 Peak foliage is moving south, bringing brilliant color to the Maine coast, New Hampshire’s Lakes Region, and Connecticut. Find out where to catch the best color this weekend, which areas are past peak, and where the show is just getting started.

📣 And remember: “Past peak” doesn’t mean the color is gone! There’s still plenty of fall beauty to enjoy.

How’s it looking out your window?

Read the full report from Jim Salge Photography (updated weekly): https://bit.ly/4Al5pak

10/11/2026

🍂 We’re glad we live in a world where they’re are Octobers…💛

10/09/2026

10/01/2026

🏆The Homestead has been named Best Bed & Breakfast on The Shoreline for 2026! This one is for YOU - our wonderful guests, friends, neighbors, and Homestead fans who voted, shared, recommended, reviewed, and cheered us on. We're so lucky to do what we do, and even luckier to have such an amazing community behind us. ❤

Thank you for making The Homestead a place worth coming home to. 🏡☕

09/29/2026

☕It's National Coffee Day!☕
That's a holiday we were born to celebrate. At The Homestead, coffee isn't just coffee. It's the smell that gets you out of bed, the first "good morning" of the day, and - if you're lucky - one of Ray's cappuccinos. 😊

If you've been a guest, you know that Ray has a way with that espresso machine! Perfect foam, just the right amount of richness, and somehow it tastes even better when you're sipping it here. 🤎

So here's to good coffee, slow mornings, and the people who know how to make a really great cup.

Happy National Coffee Day! ☕ Come to The Homestead, stay for the coffee... and definitely ask Ray to make you a cappucino.

09/26/2026

🍂 Experts say Connecticut could be one of the best places to see fall foliage this year—and there’s still time to plan your visit. Don’t miss out – the maples are expected to be especially colorful this year, and if conditions remain favorable, the fall display could last several weeks.

Check out this interactive fall foliage report map created by the DEEP (Connecticut Department of Energy and Environmental Protection): https://storymaps.arcgis.com/stories/37fd12fa3a7e46b0ba0da404496cb0ea

Use it to plan your trip to see us and the stunning colors of nature. It will help you find the best fall drives, hiking trails, and scenic views.

09/23/2026

Come see why Fall is our time to shine 🍁🍂