Guidebook for Wilmington, VT

Abigail
Guidebook for Wilmington, VT

Food Scene

Dot's is a local favorite. It's a short drive from the cabin and right on Main Street near several cute shops. The menu is classic diner fare -- good quality and good prices. It's family friendly and has an OK selection of beer and wine. They're open for breakfast, lunch, and dinner; but they close at 8pm during the week and 9pm on weekends. Closed Mondays. Can get busy - if there's a wait, we'd recommend MLT, Jezebels, or Village Roost.
106 locals recommend
Dot's
3 W Main St
106 locals recommend
Dot's is a local favorite. It's a short drive from the cabin and right on Main Street near several cute shops. The menu is classic diner fare -- good quality and good prices. It's family friendly and has an OK selection of beer and wine. They're open for breakfast, lunch, and dinner; but they close at 8pm during the week and 9pm on weekends. Closed Mondays. Can get busy - if there's a wait, we'd recommend MLT, Jezebels, or Village Roost.
The Village Roost is an informal cafe / restaurant right on Main Street near several cute shops. They have great coffee and all natural sandwiches, salads, soups, and baked goods. Most, if not all, of their food is organic. It's a casual place - you order at the counter and they bring you your food. It's a little pricey for an informal spot, but high quality. The room in the back has board games and a few comfy chairs - you can sit and drink your coffee as long as you like.
46 locals recommend
The Village Roost
20 W Main St
46 locals recommend
The Village Roost is an informal cafe / restaurant right on Main Street near several cute shops. They have great coffee and all natural sandwiches, salads, soups, and baked goods. Most, if not all, of their food is organic. It's a casual place - you order at the counter and they bring you your food. It's a little pricey for an informal spot, but high quality. The room in the back has board games and a few comfy chairs - you can sit and drink your coffee as long as you like.
The Last Chair is a great place for families and big groups (not for those wanting a quiet dinner out). It's about a 12 minute drive from the cabin over in Dover, VT. The menu is traditional american and decent (they also have pizza), but the main reason it's good for families is the "kid zone" - a huge arcade with video games, skee ball, air hockey, etc.
130 locals recommend
The Last Chair Bar & Grill
267 Vermont Rte 100
130 locals recommend
The Last Chair is a great place for families and big groups (not for those wanting a quiet dinner out). It's about a 12 minute drive from the cabin over in Dover, VT. The menu is traditional american and decent (they also have pizza), but the main reason it's good for families is the "kid zone" - a huge arcade with video games, skee ball, air hockey, etc.
In summer Wahoo's is a must. It's a little roadside stand just up the road on 100 that serves fantastic burgers and hot dogs, as well as a few unexpected natural and vegetarian items. They also have great ice cream. If you're getting soft-serve, I strongly advise getting a "small" -- the "regular" is enormous. :)
31 locals recommend
Wahoo's
2 Whites Rd
31 locals recommend
In summer Wahoo's is a must. It's a little roadside stand just up the road on 100 that serves fantastic burgers and hot dogs, as well as a few unexpected natural and vegetarian items. They also have great ice cream. If you're getting soft-serve, I strongly advise getting a "small" -- the "regular" is enormous. :)
Anchor is a really solid seafood spot. Their dinner menu is a bit on the pricier side ($20-$40 mains), but the lunch menu is very affordable. It's kid-friendly and has Fiddlehead IPA on tap, among other great craft brews.
68 locals recommend
Anchor Seafood Restaurant
8 S Main St
68 locals recommend
Anchor is a really solid seafood spot. Their dinner menu is a bit on the pricier side ($20-$40 mains), but the lunch menu is very affordable. It's kid-friendly and has Fiddlehead IPA on tap, among other great craft brews.
Maple Leaf Tavern is a great little spot. Definitely more of a restaurant than a bar. Their dinner menu is a bit pricey for a tavern, but the quality of the food is really quite high and if you're on a budget - their burger is great and reasonably priced. Wings are great too. The on-tap beer selection is solid.
66 locals recommend
Maple Leaf Tavern
3 N Main St
66 locals recommend
Maple Leaf Tavern is a great little spot. Definitely more of a restaurant than a bar. Their dinner menu is a bit pricey for a tavern, but the quality of the food is really quite high and if you're on a budget - their burger is great and reasonably priced. Wings are great too. The on-tap beer selection is solid.
Jezebel's is a quirky spot, but the food is really outstanding. My favorite are the sweet potato fries with maple sour cream dipping sauce! Their sandwiches are great, chicken pot pie, you name it.
30 locals recommend
Jezebel's Eatery
28 W Main St
30 locals recommend
Jezebel's is a quirky spot, but the food is really outstanding. My favorite are the sweet potato fries with maple sour cream dipping sauce! Their sandwiches are great, chicken pot pie, you name it.
Good little Mexican restaurant with a fun atmosphere. Family-friendly and nice outdoor seating.
50 locals recommend
La Casita
14 S Main St
50 locals recommend
Good little Mexican restaurant with a fun atmosphere. Family-friendly and nice outdoor seating.
Truly outstanding cinnamon buns and other treats. It's a bit of a drive from our place, but on the way to Mount Snow!
91 locals recommend
Sticky Fingers Bakery
210 Vermont Rte 100
91 locals recommend
Truly outstanding cinnamon buns and other treats. It's a bit of a drive from our place, but on the way to Mount Snow!
Southern Vermont isn't famous for its pizza and while most of the local spots are fine, they aren't outstanding. We think Tony's is the best and well-worth the drive from our place.
16 locals recommend
Tony's Pizza
194 Vermont Rte 100
16 locals recommend
Southern Vermont isn't famous for its pizza and while most of the local spots are fine, they aren't outstanding. We think Tony's is the best and well-worth the drive from our place.
La Toscanella serves a more personal-pan style Italian pizza with lots of vegetarian options for toppings. Super tasty, but if you're looking for mozz sticks and chicken parm, go next door to Tony's.
22 locals recommend
Pizzeria La Toscanella
148 Vermont Rte 100
22 locals recommend
La Toscanella serves a more personal-pan style Italian pizza with lots of vegetarian options for toppings. Super tasty, but if you're looking for mozz sticks and chicken parm, go next door to Tony's.
Alpenglow is a high-end restaurant open for dinner Thursday - Sunday and brunch on weekends. We've been for both brunch and dinner and highly recommend it for an upscale meal nearby. Reservations are recommended on holiday weekends in particular.
14 locals recommend
Alpenglow Bistro
9 West Main Street
14 locals recommend
Alpenglow is a high-end restaurant open for dinner Thursday - Sunday and brunch on weekends. We've been for both brunch and dinner and highly recommend it for an upscale meal nearby. Reservations are recommended on holiday weekends in particular.
Sawmill Bar and Table is a lovely restaurant within an inn over in West Dover (about 15 minutes drive). We highly recommend it for upscale dining and farm-to-table meals. They're open for breakfast and dinner (closed Wednesdays).
16 locals recommend
Sawmill Bar & Table
7 Cross Town Road
16 locals recommend
Sawmill Bar and Table is a lovely restaurant within an inn over in West Dover (about 15 minutes drive). We highly recommend it for upscale dining and farm-to-table meals. They're open for breakfast and dinner (closed Wednesdays).

Parks & Nature

The trail head is just up the road from the cabin (5 minute drive or about 40 minute walk). The hike itself is a 4.0 mile out and back (not a loop) trail to the summit of Haystack Mountain with about 1000 feet elevation change, classified as "moderate" by All Trails (you can get more reviews and info on their website). Depending on the hiker, it may take 2-3 hours round-trip. We love this hike because of its proximity to the house (obviously), but also because you rarely run into any other hikers. There are gorgeous views from the summit.
17 locals recommend
Mount Haystack Trail
184 Upper Dam Rd
17 locals recommend
The trail head is just up the road from the cabin (5 minute drive or about 40 minute walk). The hike itself is a 4.0 mile out and back (not a loop) trail to the summit of Haystack Mountain with about 1000 feet elevation change, classified as "moderate" by All Trails (you can get more reviews and info on their website). Depending on the hiker, it may take 2-3 hours round-trip. We love this hike because of its proximity to the house (obviously), but also because you rarely run into any other hikers. There are gorgeous views from the summit.
The Valley Trail connects the villages of Wilmington and Dover. The southern end of the trail is located off Route 9 in the center of Wilmington across from Reardon’s Crossing Bridge - the northern end terminates at Mount Snow in Dover. Nine trailheads and parking areas along the way and several spurs off the main trail enable users to hike all or part of the trail. One "easy" option: at the trail junction across the bridge in town, the Riverwalk splits into two footpaths forming a small loop that takes 5 minutes to walk. At the top of the loop, hikers can turn right and follow the trail for 1.5 miles to Harriman Reservoir.
Valley Trail
Valley Trail
The Valley Trail connects the villages of Wilmington and Dover. The southern end of the trail is located off Route 9 in the center of Wilmington across from Reardon’s Crossing Bridge - the northern end terminates at Mount Snow in Dover. Nine trailheads and parking areas along the way and several spurs off the main trail enable users to hike all or part of the trail. One "easy" option: at the trail junction across the bridge in town, the Riverwalk splits into two footpaths forming a small loop that takes 5 minutes to walk. At the top of the loop, hikers can turn right and follow the trail for 1.5 miles to Harriman Reservoir.
There are several trails throughout the park, but the Mount Olga Trail is great for all skill levels. The hike is an easy 1.6 mile loop (469 feet elevation change) that features a fire tower with a 360-degree view of southern Vermont and northern Massachusetts. The trail leaves the picnic area from the right side of the ranger cabin - you can ask around there for assistance. The park entrance is about a 12 minute drive from the cabin, east on Route 9 (also a gorgeous drive).
53 locals recommend
Molly Stark State Park
705 VT-9
53 locals recommend
There are several trails throughout the park, but the Mount Olga Trail is great for all skill levels. The hike is an easy 1.6 mile loop (469 feet elevation change) that features a fire tower with a 360-degree view of southern Vermont and northern Massachusetts. The trail leaves the picnic area from the right side of the ranger cabin - you can ask around there for assistance. The park entrance is about a 12 minute drive from the cabin, east on Route 9 (also a gorgeous drive).
This is the closest beach access to our house (about 10 min drive). It's a beautiful picnic area right on the water, with plenty of space in the sun for picnic blankets; as well as several picnic tables and charcoal grills that are all open to the public. There are stone steps to get down into the water. It's sunniest in the morning until about 1 or 2pm and some prefer to wear water shoes when swimming in the lake, because of the rocks. Floats and inner-tubes are always a great idea! For the adventurous: if you keep walking down the service road, past the main picnic area there is a rope swing into the water.
7 locals recommend
Mt. Mills West Picnic Area
1 Woods Rd
7 locals recommend
This is the closest beach access to our house (about 10 min drive). It's a beautiful picnic area right on the water, with plenty of space in the sun for picnic blankets; as well as several picnic tables and charcoal grills that are all open to the public. There are stone steps to get down into the water. It's sunniest in the morning until about 1 or 2pm and some prefer to wear water shoes when swimming in the lake, because of the rocks. Floats and inner-tubes are always a great idea! For the adventurous: if you keep walking down the service road, past the main picnic area there is a rope swing into the water.
One of several lakefront parks for beach access and picnics along the Harriman Reservoir. Also known as "Ward's Cove" - this is a really lovely spot. There are 10-12 picnic sites, each with picnic table and grill and a small beach. Note that if you walk through the woods 5-10 minutes past the main picnic area there is a nude sunbathing area. As with other lake beaches - it is advisable to wear water shoes (Tevas, etc.) to avoid hurting your feet on the rocks.
12 locals recommend
The Ledges
Ward's Beach Access Road
12 locals recommend
One of several lakefront parks for beach access and picnics along the Harriman Reservoir. Also known as "Ward's Cove" - this is a really lovely spot. There are 10-12 picnic sites, each with picnic table and grill and a small beach. Note that if you walk through the woods 5-10 minutes past the main picnic area there is a nude sunbathing area. As with other lake beaches - it is advisable to wear water shoes (Tevas, etc.) to avoid hurting your feet on the rocks.
Also known as "Mt Mills East" picnic area, this lake-access park is directly across the water from "Mt Mills West" and has an abundance of picnic facilities. Note - due to its close proximity to the boat launch, the area can be a bit crowded.
6 locals recommend
Swimming Area at Harriman Reservoir
6 locals recommend
Also known as "Mt Mills East" picnic area, this lake-access park is directly across the water from "Mt Mills West" and has an abundance of picnic facilities. Note - due to its close proximity to the boat launch, the area can be a bit crowded.
Jamaica state park is a really lovely state park to visit in spring, summer, and fall. It's about a 30-minute drive from our house. There are: picnic facilities, overnight camping, a nature center with programs for children, and several hiking trails. The old West River Railroad trail is universally-accessible and great for easy walking, jogging or biking. Open to all foot travel and bicycles. The trail meanders along the West River, following the old bed of the West River Railroad. The trail is stroller-friendly.
134 locals recommend
Jamaica State Park
48 Salmon Hole Ln
134 locals recommend
Jamaica state park is a really lovely state park to visit in spring, summer, and fall. It's about a 30-minute drive from our house. There are: picnic facilities, overnight camping, a nature center with programs for children, and several hiking trails. The old West River Railroad trail is universally-accessible and great for easy walking, jogging or biking. Open to all foot travel and bicycles. The trail meanders along the West River, following the old bed of the West River Railroad. The trail is stroller-friendly.
Grout pond recreation area is a great spot with picnic facilities, several hiking trails, swimming, and overnight camping. It's about 30 min drive from our place and is truly a hidden gem.
55 locals recommend
Grout Pond
55 locals recommend
Grout pond recreation area is a great spot with picnic facilities, several hiking trails, swimming, and overnight camping. It's about 30 min drive from our place and is truly a hidden gem.
Timber Creek has groomed cross country ski trails as well as snowshoeing trails and rents equipment for adults and children.
21 locals recommend
Timber Creek Cross Country Ski
13 Tanglewood Rd
21 locals recommend
Timber Creek has groomed cross country ski trails as well as snowshoeing trails and rents equipment for adults and children.

Essentials

River Valley Market (about 10 min drive from the cabin) is a small, locally-owned grocery store with all the basic essentials you need, plus a very nice selection of local, Vermont products (cheeses, cured meats, etc.). They also have a good selection of beer and wine. Some items are more expensive here than at Shaw's Supermarket, but the atmosphere is more pleasant.
51 locals recommend
River Valley Market
661 Vermont Rte 100
51 locals recommend
River Valley Market (about 10 min drive from the cabin) is a small, locally-owned grocery store with all the basic essentials you need, plus a very nice selection of local, Vermont products (cheeses, cured meats, etc.). They also have a good selection of beer and wine. Some items are more expensive here than at Shaw's Supermarket, but the atmosphere is more pleasant.
Shaw's Supermarket is a 7 minute drive away, through town. It's the closest supermarket and also has a Redbox DVD rental kiosk out front (accessible 24 hrs). The store is open every day from 7am to 9pm.
73 locals recommend
Shaw's
97 E Main St
73 locals recommend
Shaw's Supermarket is a 7 minute drive away, through town. It's the closest supermarket and also has a Redbox DVD rental kiosk out front (accessible 24 hrs). The store is open every day from 7am to 9pm.
This beer, wine, and liquor market has a great selection and even has local brews on tap. You can borrow the growler from our house (it's in the kitchen cupboard) and fill it up at Ratu's. Beer drinkers can't visit Vermont without sampling the local brews!
15 locals recommend
Ratu's Liquor & Market
34 W Main St
15 locals recommend
This beer, wine, and liquor market has a great selection and even has local brews on tap. You can borrow the growler from our house (it's in the kitchen cupboard) and fill it up at Ratu's. Beer drinkers can't visit Vermont without sampling the local brews!

Drinks & Nightlife

Short drive from the house. Classic pub with decent bar food. Thursday open mic night and Friday karaoke. Generally showing whatever football, hockey, or baseball game is on. Open until 2am.
Wilmington Village Pub
7 S Main St
Short drive from the house. Classic pub with decent bar food. Thursday open mic night and Friday karaoke. Generally showing whatever football, hockey, or baseball game is on. Open until 2am.
Short drive from our cabin on route 9, this brewery sits up on a hill overlooking the "100-mile view" on Hogback Mountain. The beer is pretty good (not the best you'll find in Vermont, by any means, but good), but the view is unbeatable. The food is really outstanding, though. Andrzejs Polish Kitchen sets up in a food truck outside and it's really extremely delicious and authentic Polish food. The bar also serves wine, is family-friendly, and is dog-friendly.
54 locals recommend
Beer Naked Brewery
7678 VT-9
54 locals recommend
Short drive from our cabin on route 9, this brewery sits up on a hill overlooking the "100-mile view" on Hogback Mountain. The beer is pretty good (not the best you'll find in Vermont, by any means, but good), but the view is unbeatable. The food is really outstanding, though. Andrzejs Polish Kitchen sets up in a food truck outside and it's really extremely delicious and authentic Polish food. The bar also serves wine, is family-friendly, and is dog-friendly.
Snow Republic has become a great addition to the local bar/food scene. They have a large indoor area with bar games and a big outdoor area as well with several fire pits and adirondak chairs. Their food menu has evolved over the last year into a small, but SOLID menu. Their smashburger is excellent, as is their fried chicken sandwich and the wings are good as well! Their not the best brewery in VT by any means (the competition is pretty fierce), but their a solid local spot -- only about 5 mins away.
92 locals recommend
Snow Republic Brewery
33 Vermont Rte 100
92 locals recommend
Snow Republic has become a great addition to the local bar/food scene. They have a large indoor area with bar games and a big outdoor area as well with several fire pits and adirondak chairs. Their food menu has evolved over the last year into a small, but SOLID menu. Their smashburger is excellent, as is their fried chicken sandwich and the wings are good as well! Their not the best brewery in VT by any means (the competition is pretty fierce), but their a solid local spot -- only about 5 mins away.

Sightseeing

The "Molly Stark Scenic Byway" is 48 miles of Vermont Route 9 running from Brattleboro to Bennington. There are tons of beautiful stopping places along the way, but the Hogback Mountain overlook is just one to point out. For those that want to enjoy nature, but aren't able to get out on foot - this scenic drive is a great option.
7 locals recommend
Hogback Mountain Conservation Area
7755 VT-9
7 locals recommend
The "Molly Stark Scenic Byway" is 48 miles of Vermont Route 9 running from Brattleboro to Bennington. There are tons of beautiful stopping places along the way, but the Hogback Mountain overlook is just one to point out. For those that want to enjoy nature, but aren't able to get out on foot - this scenic drive is a great option.
Brattleboro is about a 35 minute drive east of Wilmington and a really cool town. Though still a small town (pop. about 15K) it's quite a bit more active than Wilmington. There are several nice restaurants, bars, and breweries -- and the iconic Latchis Theater, which (in addition to movies) has concerts and other special events.
94 locals recommend
Brattleboro
94 locals recommend
Brattleboro is about a 35 minute drive east of Wilmington and a really cool town. Though still a small town (pop. about 15K) it's quite a bit more active than Wilmington. There are several nice restaurants, bars, and breweries -- and the iconic Latchis Theater, which (in addition to movies) has concerts and other special events.
Bennington is about 30 minutes west on Route 9 and, similar to Brattleboro, has a bit more going on than the villages of Wilmington and Dover. There's a variety of restaurants, bars, and breweries. The 48-mile drive from Bennington to Brattleboro is one of southern Vermont's most famous scenic byways.
61 locals recommend
Bennington
61 locals recommend
Bennington is about 30 minutes west on Route 9 and, similar to Brattleboro, has a bit more going on than the villages of Wilmington and Dover. There's a variety of restaurants, bars, and breweries. The 48-mile drive from Bennington to Brattleboro is one of southern Vermont's most famous scenic byways.

Entertainment & Activities

Mt Snow is the premiere ski resort in the area. Definitely check out their website for the Snow Report and discounted Lift Tickets (often $20 cheaper than buying onsite).
47 locals recommend
Mount Snow Grand Summit Resort
89 Grand Summit Way
47 locals recommend
Mt Snow is the premiere ski resort in the area. Definitely check out their website for the Snow Report and discounted Lift Tickets (often $20 cheaper than buying onsite).