Things to do Near Chester Inn

Shops in Chester

DaVallia - Art & Design
Fischer Arts
Meditrina Wine & Cheese
Sharon’s on the Common (Clothing)
Sage Jewelry & Gifts
Wisdom River Designs
Stone House Antique Center
Vintage Vermont
The Bargain Corner (Antiques)

Matilda and Three Bears (Antiques)
Stonevillage Farmers Market
Smokeshire Designs
Six Loose Ladies Yarn & Fiber Shop
Polish Pottery Gift Shop
Sugar Bob’s Finest Kind (Maple products)
Mitch’s Maples
Down to the Roots (Cannabis)

Vermont Country Store: (2 nearby locations: Weston & Rockingham) - If you’ve never visited a Vermont Country Store, it’s definitely worth a stop! The stores are full of charm and have a wide selection - locally made food items, candy, clothing, personal care, homewares, etc.

Local Mountains

Check corresponding websites for information on lift tickets & additional seasonal activities:
Magic Mountain - estimated 15 minute drive
Okemo - estimated 19 minute drive
Stratton - estimated 31 minute drive
Killington - estimated 39 minute drive
Mt. Snow - estimated 50 minute drive

Grafton Trails & Outdoor Center - Delight in winter activities including skiing, snowshoeing, fat biking, snow tubing, and sleigh rides, or visit in the summer for mountain biking, swimming, boating and hiking. You can call (802) 843-2350 for more information / reservations.

Wineries / Breweries / Distilleries

Vermont Vines (Chester, VT) - estimated 9 minute drive
Putney Mountain Winery (Putney, VT) - estimated 31 minute drive
Outer Limits Brewing (Proctorsville, VT) - estimated 13 minute drive
Twisted Horn Brewery (limited hours - Londonderry, VT) - estimated 17 minute drive
Harpoon Brewery (Windsor, VT) - estimated 37 minute drive
Saxton’s Distillery (Brattleboro, VT) - estimated 35 minute drive
Cooper Cannon Distillery (West Chesterfield, NH) - estimated 36 minute drive
Smuggler’s Notch Distillery (Manchester, VT) - estimated 40 minute drive
Still on the Mountain (Killington, VT) - estimated 49 minute drive

Child-Friendly Activities

The Nature Museum - Grafton, VT - estimated 13 minute drive
Endless Creations (Art Center) - Chester, VT- estimated 1 minute drive
Chester Municipal Pool & Playground - Chester, VT- estimated 2 minute drive
Springfield Cinemas 3 (Movie Theatre) - Springfield, VT- estimated 14 minute drive

Breakfast Recommendations

Here are a few great spots right along Main Street…

Southern Pie Cafe - This cafe is only 300 feet away in the strip of shops right across the street. They are famous for their unique sweet & savory pies. We frequent the cafe for breakfast sandwiches and coffee. Customers also love their specialty drinks, sandwiches, pastries & homemade ice cream.

Country Girl Diner - Take a left out of the driveway and the diner is just .7 miles miles up the street. The 1940’s silver dining car has classic charm, friendly waitresses & hearty breakfasts. They serve lunch as well.

Mercantile on Main - Conveniently located right across the street, M.o.M’s bakery is always cranking out different seasonal sweets. Customers love their pastries, cinnamon rolls and fresh breads. They have various breakfast and lunch specials each day.

In Neighboring Springfield...

Maebelline’s - This popular breakfast spot offers great food & service. What sets Maebelline’s apart is its location, offering beautiful river views.

Lunch Recommendations

Smitty’s Chester Market - Just off Rt 103 (.8 miles away) is this charming local food store. Smitty’s has a deli in the back for sandwiches and paninis, and has a changing selection of hot and cold meals to go. Please note, there is no seating section in the store. This is a great stop if you want to pick up a few items or local foods for your trip in one fell swoop. Considering the size of the store, they have a huge selection of craft beers & wines. If you are using local maps to navigate your way there, you may see the old name ‘Lisai’s’ listed.

Fullerton Inn - Directly across the street, the dining room is open for lunch most days starting at 11:30am. They also offer a long list of appetizers, burgers and adult beverages. In warmer months, there is outdoor seating on the front porch. You can also view their menu online and call in for take out.

Smokin’ Bowls - This small roadside shack (open on weekends) serves up food on the go, or to enjoy at a picnic table when the weather allows it. If you love soup or smoked meats, this is your stop. Some favorites include their African peanut soup, clam chowder, chili & pulled pork.

Dinner Recommendations

Right Here in Chester...

Meditrina Wine Bar & Restaurant - This wine shop, turned bar & restaurant is conveniently located right across the street. The atmosphere has a moody vibe reminiscent of a mid-century speakeasy. Meditrina has a relatively small curated menu consisting of delicious locally sourced snacks, pizza, pasta & seafood bites. They are typically open Thursday-Sunday nights. You can also reference their facebook page for tasting events.

MacLaomainn’s Scottish Pub - The pub is located on Main Street and serves a combination of classic bar fare & delicious authentic Scottish cuisine. The staff is friendly and happy to make recommendations.

Fullerton Inn - Mentioned previously in the lunch section, Fullerton Inn is as convenient as it gets for our guests and reopens for dinner service. Many of their lunch offerings are also available at dinnertime, along with additional entrees.

The Pizza Stone - This casual restaurant offers a wide variety of stone-baked, thin crust pies crafted with local ingredients. There is a huge selection of beers & ciders on tap and there is often live music performed by local bands.

Maria’s Mexican Food - Maria’s serves out of a small shack window, but don’t let this deter you. This is authentic Mexican - tacos, burritos, tamales, sincronizadas, tortas, etc. Please note, there is no indoor seating here, as it operates similarly to a food truck. There are picnic tables outside to eat at when seasonally appropriate. Maria’s is good to keep in mind as an option at the beginning of the week when most local eateries are closed.

Our Favorite Restaurants in Neighboring Towns…

Phelp’s Barn Pub (Grafton - 13 minute drive) - This restaurant is located in a beautifully appointed barn attached to Grafton Inn. The main floor is a dining room and there is a bar and high top tables upstairs. We love the crispy brussel sprouts topped with applewood bacon, blue cheese, and a chipotle maple drizzle. The cocktails are always fantastic! They switch out entree offerings regularly, but their menu can be viewed online, as well as their schedule for live music. Reservations are not necessary, but I’d recommend making one.

Leslie’s Tavern (Bellows Falls - 14 minute drive) - Leslie's Tavern has been serving Vermont inspired fine dining since 1986. The restaurant is in a historic colonial building and has a cozy atmosphere with roaring wood stoves. Leslie makes you feel like part of the family as chef John whips up unbelievable dishes with fresh ingredients from their garden. Their chef also offers private and group cooking classes if arranged in advance. You can call or text 802-376-4050 to make a reservation.

The Copper Fox (Springfield - 13 minute drive) - The chef-owned establishment prides itself on sourcing local ingredients whenever possible. The bar area was built with 200-year-old barn wood, complete with a copper bar top. Everything we’ve tried here has been amazing - soups, dirty potatoes, specialty pizzas & complex cocktails. Live music is usually performed on Thursday nights.

*If you have food allergies or sensitivities, Country Girl Diner, The Pizza Stone & The Copper Fox all have reputations for being particularly aware & accommodating.

Near Okemo Mountain…

The Loft Tavern - As close as it gets to Okemo, locals flock to this low-key tavern after the mountain for great pub fare and drinks. In more recent years, they installed a meat smoker out back and expanded into BBQ. Their wide selection of beers also makes this a favorite among enthusiasts.

DJ’s - This family restaurant offers elevated dishes in a casual environment. There is a small bar that locals love to congregate at and 2 dining room sections. Come hungry - portions are generous and entrees are all served with bread & salad.

Killarney Irish Pub -The Killarney is a family-owned and operated pub, where locals and visitors alike come to gather in an authentic Irish atmosphere. With 5 HDTV’s and surround sound, The Killarney is a great spot to have a drink and watch the game. They have wide selections of beer (15 on draft & over 30 bottled) and scotch & whiskey. Killarney has snatched up numerous awards for their chicken wings.

Main & Mountain Bar - Typically open Thursday through Sunday, this is a great place to treat yourself to a fancy cocktail. Hang at the trendy bar inside or take a drink outside and enjoy them by the tabletop fire pits. The menu here consists of light bites so this is a great spot for apres-ski or a nightcap.

Local Hikes

Right through our backyard…
The Brookside Hiking Trial is a 1 mile loop located in the Brookside Town Forest. The trail head starts at the backside of our property. If you walk across the land to the tree line, you will spot a walking bridge. This one mile loop borders other private properties, so please be kind and stay on the trail.

Chester Town Forest…
The 550-acre Chester Town Forest, off Route 11 in Chester, Vermont, features a pair of easy/moderate , family-friendly loop trails.
- The Butternut Hill Trail (1.9 miles) leads to the top of Butternut Hill, and offers views of Vermont’s Stratton Mountain, as well as Sunapee Mountain in New Hampshire.
- The Lost Mine Loop Trail (2.2 miles) leads to the remains of an abandoned talc-mining site that operated between 1894 and the 1930’s.

Trails in nearby /neighboring towns…
Buttermilk Falls Trail
Head out on this 0.5-mile out-and-back trail near Ludlow, Vermont leading to a waterfall. Considered an easy route, it takes an average of 12 min to complete. This is a very popular area for walking, so you'll likely encounter other people while exploring. The best times to visit this trail are April through November. Dogs are welcome, but must be on a leash.

Okemo Summit Lodge Trail (via Bear Climb & Moose Trek Trail)
Head out on this 5.4-mile loop trail near Ludlow, Vermont. Generally considered a challenging route, it takes an average of 3 h 18 min to complete. This trail is great for hiking, and it's unlikely you'll encounter many other people while exploring. The best times to visit this trail are June through November. This loop begins near the Sugar House Lodge and follows the Bear Climb Trail towards the summit lodge at Okemo Mountain. The trail travels through the forest and across open ski runs that offer nice views along the way. After hanging out at the top, follow the Moose Trek Trail back to the base of the mountain.

Ludlow Mountain (via Healdville Trail)
Explore this 5.9-mile out-and-back trail near Belmont, Vermont. Generally considered a challenging route, it takes an average of 3 h 44 min to complete. This is a very popular area for hiking and snowshoeing, so you'll likely encounter other people while exploring. The best times to visit this trail are May through November. Dogs are welcome, but must be on a leash. The summit of Ludlow Mountain is also the top of Okemo Mountain Ski Resort. Just through the woods from the ski runs you will find a fire tower that offers 360-degree views of the surrounding area. The trail has plenty of exposed roots and rocks, so shoes with good traction are recommended. It is a steady climb the whole way to the tower.