Michael's on the Hill is fabulous, so you definitely can't go wrong there. I've heard wonderful things about Philo Ridge Farm, which is very much farm-to-table. The restaurant at Shelburne Farms is also quite good!

You should check out adventuredinner.com

Vermont Fine has a private upstairs banquet room and they would love to accommodate your family! I just went for my fiancés birthday; the food was brilliant and the setting was classy but mellow, not at all uptight. I encourage y’all to give the new chef-owners, Chelsea and Tom a chance to wow you! https://www.vermontfine.com

I haven't eaten at Junction (Essex Resort - they grow some of their produce and such, but they source locally for the rest), but I know they have a private dining room. I have eaten at Tavern, who also source locally, many times as it was convenient to my mom's Alzheimer's community. Tavern also has private dining in the Timber Room, but I don't know the capacity. The website for Junction says 10 people though. You could ask the Essex Resort if they can do a larger group.

Tortorelle has a private room or a barn that could work. The setting is beautiful and the food very good.

I had my rehearsal dinner at Jericho Cafe and Tavern with about 30 people and that was perfect for us! They are popular though, so I would make sure to book the party sooner rather than later.

You should look into Adventure Dinner. Awesome staff and they put out great meals in cool places across the state. I know the owner and she’s a gem too https://www.adventuredinner.com

You can't get a meal at Michaels on the hill for $25 though. That place is 16 apps and 40 entees. It is worth every penny, just not in the $25 budget.

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I think OP was referring to 25 people, not a $25 budget.

If you are willing to stretch the distance a bit, The Drake in St Albans has done private events, and the food and service is amazing.

+1 for Adventure dinner. Really unique & thoughtful events

-1 for adventure dinner. Had a valentine's dinner with my wife through adventure dinner. It was offensively overpriced even accounting for the valentine's day premium, most dishes came out lukewarm, we left hungry. Diners were pissed; one couple got up before the last course to cut their losses. My wife (who is herself a head chef at a popular farm to table restaurant in VT) tried to reach out charitably to give feedback about what went wrong, never heard back, not even a thanks for your feedback. They contract with chefs and venues, but are not themselves preparing or doing logistics, so inconsistent. And when it does go wrong, you're going to be out in the cold with a hole in your wallet.

Tldr; don't do adventure dinner. High prices guaranteed, but quality control is ymmv.

Starry night cafe in Ferrisburgh is excellent, and their entire back room (super cozy enclosed panoramic patio with a fireplace) can be reserved with enough notice. It’s a perfect space for that size party and the food/drinks are consistently excellent

Frog Hollow Farms in Hubbardton sometimes hosts dinners on their farm with all local ingredients. I bet they'd be open to arranging a private event for all of you!

It's a bit of a drive (but what isn't in this state?!)

https://www.froghollowvt.com/

Went to an event there also and it was delicious!

If you're willing to take a beautiful drive about an hour from Essex I'd recommend The Black Lantern in Montgomery. Chef Hirsch uses tons of local meat, produce, and dairy. Not just Vermont local but focused on farms in the Franklin County community.

Definitely Philo Ridge in Charlotte

I’ll offer an off-the-wall suggestion, but you’d need to act quickly to secure the time. Rent the Cabin/Pavilion space at Mt. Philo State Park and hire a local caterer. JCAT, Bevo, Bluebird, and Mark BBQ, all are excellent for great home-style eats, and y’all can mosey to some great views or spread out. The cabin and pavilion make it pretty weather proof for both the meal and caterer as well. Easy access for older folks, too.

Another cool option is the pavilion at American Flatbread in Warren, but a more limited food selection, I’d imagine.

Michael’s and HotW are excellent, hands down, I don’t think you’d be disappointed.

As a wild card, if folks are more adventurous in their palette, Sushi Maeda has a huge space and the food is incredible. Lots of local ingredients are used there in non-traditional ways. Book them early and give Mike/Paddy/Nick time to plan.

It was sad to see Kitchen Table go, but my first impression at VT Fine was solid! Which I’m stoked on since it’s less than 10 minutes from my home!

Tourterelle has been on my list for more than a decade, this reminds me that I need to make a reservation!

Thanks for this, I don’t often go up to Jay, but now I might have a reason.

Try Farmers and Foragers. They’re a food truck named best in VT, but have also set up a permanent location by the marina at the waterfront. Really wonderful to see the sun set over dinner, and their menu offerings are based on what fresh local ingredients they can get. At one point this past summer they were able to get oysters from somewhere in MA famous for their oysters (not sure where, not a fan of oysters).

Not sure if this is fitting what you’re looking for, but I hope it helps!

*Edit: the Burlington waterfront!

Try the mole chicken, it features chickens raised and processed by me! You'll also see Breezy Acres beef and pork on the menu which is less than a mile from the Lantern and it's amazing quality!

Awesome place, been twice in the past few months. Bonus, it’s where the Godfather of the small town quality VT food renaissance began, RIP Michel Mahe.

Ohh, I misread that. I thought he was looking for ~(roughly) 25 per plate. Woops.

Love me some Molé.

JCAT is always a solid choice!

Does blue paddle still do private events?

I love the inn at Shelburne farms, it’s super pricy but so is anything farm to table. The added bonus is that being at Shelburne farms is its own experience, super beautiful and you can make a whole day of exploring the farm before the meal.

Was gonna type “starry night” too. Perfect spot for your needs. Back room is great.

That’s too bad. We have a new baby now, so I mostly lust after fancy food on instagram these days rather than actually go out. I’ll be lucky if we get take out and nice wine this Valentine’s Day. 😂

Pizzeria verita

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Philo Ridge is indeed wonderful; their dinner menu ran $65pp last summer (app/main/dessert).

Am an experienced private chef and caterer... if you would be interested in renting a venue (nice air bnb?) I would love to cook for your group. I can send along resume and photos and we can talk budget, menus, service style etc. Just throwing it out there.

Thanks for this suggestion!

Fantastic, I can't wait to check this out. Thank you!

Oooh looking at the menu right now.

Will keep it in mind, thank you.

It might be a stretch for this crew this time, but my partner and I will add it to our list. Thank you.

Oops sorry, I meant 25 people.

The photos are heavenly. Omg. Exactly what I was imagining. Will be checking it out.

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Checking out all three in detail. Many thanks. Philo Ridge looks gorgeous, and at least or two others have mentioned Shelburne Farms.

Super fun idea, had not considered. Definitely a possibility as long as its accessible. Thank you!!

Hm, ok thanks for feedback. I looked at the website and it's a fun idea but probs out of reach for this kind of thing -- looks like $3500 and up to start with for private events.

I take it back we have gone out exactly once during our visits to Essex and it was to the Jericho Cafe and Tavern for brunch years ago. Very memorable! Will consider, thank you.

Thanks for offering, we'll keep this in mind. I appreciate the reply.

We're not too far from Junction, I'll pop by and take a look.

Thanks for the rec!

Thank you, a few folks have mentioned and I'm definitely checking it out!

Oh I've heard the name, but never tried it. Must be the truck. Will take a look at the brick and mortar. Thank you. Maybe the oysters were from Duxbury MA, from Island Creek ;)

Fable Farm!