The Hum Before the Hush
by Elizabeth on October 04, 2025
We have maybe two more busy weekends like this before that hush settles in—the season you heard about in the song called "stick season." But right now, we're still in the thick of fall, and the inn is humming.
It's a funny time of year, though. The days are still full of guests and conversation, but there's a quiet undercurrent of change. This fall, that feeling is stronger than usual because we're in a bit of a waiting season ourselves. We have an offer on the inn (which is both exciting and surreal), and we're waiting to see if it all comes together. Other potential buyers are still reaching out and taking tours at the same time, something that makes us feel a little more confident we will be out of the inn before too long, while still trying to stay patient—keeping the fires lit, the rooms ready, and the coffee flowing while we wait to see what's next.
As we head toward winter, we're planning to take it slow through the holidays and really be present as a family. And we've decided that if we're going to open the inn at all this season, we want to go big—or not at all. So we're focusing on group bookings only for November and December.
Honestly? We've discovered how much we love that dynamic. A bus rolling in at night. A team meeting around the breakfast table. Everyone heading out to the Snow Bowl or Rikert in the morning, then coming back cold and hungry and full of stories. There's something deeply satisfying about seeing the whole inn come alive around a shared purpose. It's easier for us, too—one check-in, one rhythm, one big burst of energy instead of the stop-and-start of individual reservations. We wanted to see what it would bring us, and so far, it's brought exactly the kind of winter we're hoping for.
If your group, team, or retreat is looking for a cozy Vermont inn this winter, now's the time to reach out. Chipman Inn, in the heart of Ripton, Vermont, sits just minutes from Middlebury College, the Middlebury Snow Bowl, and Rikert Nordic Center—perfect for ski teams, writing groups, and winter getaways in the Green Mountains. Our calendar is open, and we're ready.
For now, though, I'm soaking in every last bit of this peak color before the world turns quiet and still again. Stick season always brings its own kind of beauty—subtle, soft, and full of anticipation. But today? Today the trees are still burning bright, and the inn is full of voices, and I'm grateful for both.
Middlebury College Family Weekend: Finding Accommodations When Everything's Booked- and OTA's are failing you
by Elizabeth on September 13, 2025
Planning for Middlebury College Family Weekend and finding that every hotel, B&B, and inn is already booked? You're not alone. This popular Vermont weekend fills up months in advance, leaving families scrambling for what feels like a last-minute request—even when you start looking three months ahead.
Creative Solutions for Middlebury Family Weekend Lodging
When traditional inns and hotels are sold out, here are alternatives to consider:
Explore Unique Camping Options
Hipcamp offers more than tent camping—look for RV spots (we have three at Chipman Inn where you can still order breakfast and coffee), rustic cabins, or quirky spots you won't find on Hotels.com. Think something different—composting toilets, yurts, bring-your-own-linens, or no Wi-Fi—but still with a hot shower and close to campus. Some people just post their backyard apartment to the "hip" laidback clientele of Hipcamp.
You can sign up and start with $10 in Hipcamp cash: https://hipcamp.com/i/chipmaninn (and yes, I get $10 too—shameless plug!)
Or, if you're thinking "Wait, I have land! I should be a Hipcamp host," tell them I sent you by: https://hipcamp.com/r/chipmaninn
Tap Into Your Student's Network
Professors and community members sometimes host families in their homes. I know of at least one professor who opened rooms in his house free of charge. Others may know a friend with a guest room who is happy to host Middlebury parents for a minimal cost—but who wouldn't want to list on Airbnb and risk complete unknowns in their home.
Create Your Own Family Weekend
Last year, a group of parents whose kids were all friends booked out the inn on a non-peak weekend to avoid the crowds and enjoy time together. It was their own version of Family Weekend, and they loved it. We had a caterer come in so they could enjoy a long meal together in the homestyle comfort of our inn, and they got easy reservations at restaurants for other meals—without fighting the crowds.
Planning Ahead for Future Family Weekends
If you're already thinking about next year, here's how to improve your chances:
- Start early: For 2026 Family Weekend, begin your search in late fall of this year—most properties begin taking reservations and waitlists as soon as they are filled
- Book directly with Vermont B&Bs to avoid OTA issues
- Join accommodation waitlists as soon as you can
- Explore RV and camping options in Addison County
- Coordinate with other families for group bookings
Why Online Booking Sites Sometimes Let You Down
Online travel agencies (OTAs) like Airbnb, Expedia, or Hotels.com can help—but sometimes they're a necessary evil. Our favorite OTA is Airbnb. Comedian Mike Birbiglia jokes in his Netflix special Old Man in the Pool that Airbnb is a "wildly inaccurate acronym"—because there's no breakfast... it's one of the letters. However, at Chipman Inn, there's definitely a great breakfast if you desire.
If you've had a reservation canceled through an OTA, it might not be the property's fault. These platforms regularly have technical glitches that double-book rooms or show availability when the business is already full.
At Chipman Inn, we recently experienced just that. On a major OTA, a calendar sync error showed our rooms as available for Family Weekend—even though we've been booked for that weekend for months and have a waitlist 12 families (and counting) deep.
I spoke with one parent who thought she had lucked into her choice of six open Chipman Inn rooms, only to be told by Expedia that her reservation was quickly canceled. To make matters worse, they relocated her to a hotel an hour and a half away, and now she can't get out of that booking.
Word of Advice
Anytime you book through an OTA, take a moment to check the business' direct website. Direct bookings are often cheaper (at Chipman Inn, up to 50% less!) and the funds go directly to small, local business rather than large corporations. At our inn, you'll see the 11-year-old whose ballet lessons your reservation helped support. You may see our housekeeper, who takes joy in the details—fresh linens, spotless rooms, and a warm, quiet presence that makes every guest feel cared for. She takes pride in her work, and it always brightens her day when she finds a small token of gratitude left for her to buy a special treat for her 5-year old on the way home that day.
Family Weekend is about being with your student and making memories. Whether you stay in a cozy inn, an RV, or a borrowed guest room, the time together is what matters most.
If you're looking for authentic Vermont hospitality near Middlebury College, consider booking directly with local inns like Chipman Inn. It's the most reliable way to secure a reservation—and you'll always be welcomed like family.