Who is ready to ski and ride Killington this winter? We sure are!! Below is our operating plan for the 2024 - 2025 season.
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Cleaning: 
We will NOT be entering rooms after check-in for room service.  We are happy to do a towel swap for stays longer than 2 nights should you need clean towels, toiletries or trash/recycles removed.

Breakfast:
Our continental breakfast is included daily with main inn lodging reservations.  We are continuing to have individually wrapped items and more "grab and go" type of options.  We will also be providing a self-serve coffee and tea station in our Great Room.  For weekdays, breakfast will be served from 7:30 to 9:30. For weekends & peak weekdays, breakfast will be served from 7:00 to 9:00. Breakfast and coffee service will NOT be provided to guests staying in our guesthouse.

The Guesthouse (Barn/Loft):
- Occupants of our Guesthouse (Barn and Loft) will NOT have access to the main inn or its amenities through the 2024 - 2025 ski season.  Breakfast and coffee service will NOT be provided to these units. The Guesthouse, Barn and Loft are private, standalone rental units.

If you plan on skiing or riding at Killington or Pico, please make sure to know their winter operating plan. Click here for all the details!  
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It is your responsibility to be aware of our booking and cancellation policies.  We are strict in our cancellation policy. Click here for our reservation policies.

Please call us at 802-422-8800 with any questions. ​

Super fun, super stylin', super sassy, super REAL, unfiltered & unapologetic...Haley & Zac brought it all to Trailside Inn for their early September wedding weekend! What an absolute BLAST had by all.

​​Friday Catering: Caja Madera 
Wedding/Brunch Catering: Vermont Farms Catering
Rentals: Celebrations
Linen: The Linen Shop
Floral: Flower Power VT
Photo: Eaton Photography 
Hair/Makeup: JW Artistry
Entertainment: Jurassics Sound & Light​
Transportation: Tri-State

August in Vermont can mean the best of both worlds - still so green & vibrant, but cooler nights with a "Fall feel". Jaime & Mike brought together the best of their worlds; their family, their friends for a classically beautiful event!

​​Friday Catering: Caja Madera 
Wedding/Brunch Catering: Vermont Farms Catering
Rentals: Celebrations
Linen: Linen Shop
Floral: Pittsfield Garden Center
Photo: Duback Photography
Entertainment: Wedding DJ VT - Evan 
Hair and Makeup: Heather Garrow Studio

Sometimes it is all in the details. An East Coast wedding for a West Coast located Hannah & Scott...well, they made it look easy. Lovely, thoughtful, refined and beautifully composed, their weekend was simply stunning.

​​Friday Catering: Caja Madera 
Wedding Catering: Black Diamond 
Rentals: Celebrations
Linen: The Linen Shop
Floral: New Leaf Organics
Photo: Ben Wheeler Photography 
Entertainment: Wedding DJ VT
Hair/Makeup: Nomad’s Creative Corner / M.I.L.A. Beauty
Transportation: Tri-State

Attentive & gracious selections came together so seamlessly for Lindsay & James' early August wedding. It just all felt so right.

​​Friday Catering: Caja Madera 
Wedding Catering: Black Diamond 
Rentals: Celebrations
Linen: The Linen Shop
Floral: Pittsfield Garden Center
Photo: Gold Wing Photography
Entertainment: Wedding DJ VT
Hair/Makeup: Beauty Art by Natalia / Leah Francesca Makeup

A few light sprinkles couldn't slow down Mary Charlotte & Rob's party. It was all smiles for this crew on their June weekend that included special elements like a morning yoga session and a caffeine delight coffee bar!

​​Friday Catering: Caja Madera 
Wedding/Brunch Catering: Vermont Farms Catering
Rentals: Celebrations
Linen: Linen Shop
Floral: DIY
Photo: Northeastern Photography
Hair and Makeup: LanieMax Hair / Courtney Rose
Hair/Makeup: Trish Sullivan (Boston) / Five Elements

We are beyond excited to welcome wedding couples & guests to Trailside for this Summer and Fall! We want to make sure that our couples, guests and vendors have a great party.

Below are some details for the wedding weekend. Specific wedding details can be found on the couple's wedding websites and invitations.

- We will be offering our continental breakfast daily with lodging reservations. Breakfast timing is based on the event and available on our schedule board when you arrive.

- Check-In time is 4:00pm. Check-Out time is 11am. Click here for our reservation policies.

- We will NOT be entering rooms after check-in for room service.  We are happy to do a towel swap or take trash/recycling from the room, if desired.

- Outside events and gatherings will end at 10 PM due to a local noise ordinance. Our interior commons spaces close at 1 AM nightly. Please be respectful to everyone on property.

- ​​Smoking & Vaping are not allowed anywhere inside of our buildings.

- The Cocktail Hour and Reception events will be serviced by a licensed caterer and bartender.
During this time (~3 PM to 10 PM) only drinks provided by the caterer / bartender may be consumed. NO outside / personal alcohol may be brought into the Cocktail Hour / Reception spaces. Any breach of these rules may cause an immediate shutdown of the event as this would violate Vermont liquor laws.

- Please be cognizant of yourself. If excessive drinking leads to rude, unsafe or damaging behavior, guests will be required to leave the property immediately without refund.

- We will be at capacity for the weekend, so please park respectfully in marked spaces to make sure there is enough room for everyone.

- Ceremony & Cocktail Hour are on grass, so flat shoes or wedges are suggested

- Vermont evenings can get chilly - you'll want to bring a jacket or your favorite hoodie with you.

- All offsite guests must depart the property at 10PM for all days.  Only onsite guests can attend the onsite afterparty.

Please contact us at 802-422-8800 or [email protected] with any questions.

Oh what a weekend full of adventure! Beginning with an Italian themed wood-fired pizza party, Molly & Lex's events continued with a Summer wedding in Fall, a comfort food (and dessert!) feast for cocktail hour + reception, rounded out by a glow stick dance party! Such a fun way to wrap up the 2024 Trailside wedding season.

​​Friday Catering: Farmers Market Pizza 
Wedding Catering: Vermont Farms Catering 
Dessert: Vermont Farms Catering
Rentals: Celebrations
Linen: The Linen Shop
Floral: Pittsfield Garden Center
Photo: Clove Hitch​
Hair: Shear Cuts
Entertainment: Wedding DJ VT
Transportation: Tri-State

Flannel Friday kicked things off and those chill vibes continued throughout Emily & Andrew’s Autumn wedding weekend. No strangers to Trailside, this couple knew how to make memories for their guests; creating an unforgettable gathering for their family & friends.​

​Friday Catering: Open Hearth Pizza
Wedding Catering: Vermont Farms Catering
Rentals: Celebrations
Linen: The Linen Shop
Floral: DIY
Photo: Lafleur Photos
Hair/Makeup: Five Elements Salon and Spa,  Sweet Face Makeup (Molly)
Music/Photobootht: Foley Weddings