We're going to be spending 5 days in Ascutney, VT. I'm looking for suggestions for a couple of great "upscale" restaurants, as well as a couple of nitty-gritty, regional-food favorites (like recommending good cheesesteak joints in Philly, where I'm from.) Anything within 20-30 miles would be greatly appreciated.
You don't mention when you'll be there, but assuming it's this fall, before the snow flies, driving thirty miles is going to mean close to an hour's drive (if it's after the snow flies, it could be longer) from Ascutney because it's not near any really major roads. It's state highway all the way. Also, how long it takes might depend on if you're going north/south or east/west. Just something to keep in mind when you're looking at different places to eat.
As I recall there is nothing that could be considered fine dining either in or very close to Ascutney. There's a McDonald's and, IIRC, the ubiquitous "village pizza place" that all the towns seem to have. You're going to have to travel to get to some decent meals.
Here's a thread that has some decent recommendations:
I strongly recommend you look at a map before deciding to go to any of these places, especially a map that shows you the lay of the land. Generally, in Vermont, going east/west means you're crossing mountains, which means more slow-going twisty up and down roads. North/south the roads are still twisty but more flat and with spots for faster driving, and also usually in better shape than the ones over the mountains.
Ascutney is, fortunately, near Interstate 91, so that can get you up to Hanover, NH and other places with real food somewhat quickly.
Two nicer suggestions:
Burdick in Walpole
Simon Pearce in Queechee
You're not too far from Hanover/WRJ area, and up here I'd suggest:
Tip Top in WRJ
Canoe Club in Hanover
Yama in Hanover
27 S Main St, Hanover, NH 03755
96 Main St, West Lebanon, NH 03784
Tip Top Cafe
85 N Main St Ste 100, White River Junction, VT 05001
Simon Pearce Restaurant
1760 Quechee Main St., Quechee, VT 05059
Not too far from Ascutney is Claremont, NH. This is somewhat of a 'gritty' new england mill town. However, it's trying to reinvent itself. the cornerstone of this project is the new Common Man restaurant in an old mill complex. No expense was spared putting this very beautiful eatery in an old run down complex of mill buildings. Very beautiful setting on a rushing river. The food is quite good also.
You'll find many good restaurants in the Hanover/Lebanon area. A real fun one is Three Tomatoes Tratoria on the Lebanon Green - interesting, not typical Italian fare. For something really different, there's a tiny byob Cambodian place on the eastern end of Woodstock called Angor Wat. First rate Asian food in a very casual atmosphere.
For gritty and local, there's Daddypops Tumble Inn diner in Claremont. Not sure if they are open in the evenings.
Favorite "local" eateries include:
Keeper's Country Cafe - down the street in Reading; great local dinners
Stella's - 10 minutes in Hartland; best breakfasts and lunches
Skunk Hollow Tavern- 10 minutes in Hartland; eat in the pub; wonderful local music
South Woodstock General Store - 15 minutes,beautiful drive; breakfast and lunch - great
Allechante - Woodstock; pastries, sandwiches, prepared gourmet deli items
Barnard Inn - Barnard, 30 minutes; tavern menu preferred; great localvore selections
Dana's by the Gorge - Quechee; 30 minutes; breakfast and lunch great before or after walk down to the Gorge
Parker House Inn - Quechee; Euro - style bistro; good food
Quechee Inn - Quechee; Old NE inn atmosphere; great food
Dana's by the Gorge
5945 Woodstock Rd, White River Junction, VT 05001
Barnard Inn Restaurant
, Barnard, VT 05031
61 Central St, Woodstock, VT 05091
In Ascutney, you are very lucky to be within a short drive to the best dining experience in the area...the Inn at Weathersfield (right on route 106 in Weathersfield). The emphasis is on local, fresh food. The chef is inventive. Your mouth will be glad you went. I agree with greenstate on Keepers in Reading, also on rte. 106, a little north of Inn at Weathersfield. I was just there again last week...had their bangers and mash. What is so great about this place is they really pay attention to their sides...great spinach with the bangers. I never worry when I bring guests there. A little further north on 106 is the Kedron Valley Inn in South Woodstock, a wonderful old inn with a great old bar area, (right near the South Woodstock Country store which is a great stopping place for lunch). Ascutney is close to Windsor which has a few dining places that get some good reviews: Juniper Hill Inn (stately, large old Inn at the top of the hill-- great views), Windsor Pub (I think it's the same ownership at the Juniper Hill Inn -- or was at one time) and an African place called Miriam's which is right on the main street and I am itching to get there one day. Just over the Conn. river (across the longest covered bridge in the US) is Plainfield, NH, home to the Home Hill Inn...another beautiful Inn in a beautiful setting...has a special Sunday brunch, too. Let us know what you decide!