Last Cup Cafe
87 State St, Rutland
One of my two coffee answers. It is always a tie between here and Speakeasy, so I am listing both. Great lattes, including a salted maple one, and an easy stop on State Street.
Eat & Drink
Coffee, breakfast, lunch, dinner, and something sweet.
Speakeasy Café
31 Center St, Rutland
The other half of my coffee tie. Right on Center Street downtown, so it pairs well with a walk and some shopping.
Birdseye Diner
590 Main St, Castleton
My breakfast pick when I want a real diner breakfast. Worth the short drive to Castleton.
Morningside Bakery
37 Center St, Brandon
My Brandon breakfast and brunch pick. Baked goods, wood fired pizza, and provisions on Center Street.
Taco Fresco
56 Center St, Rutland
My go to lunch in Rutland. Quick, fresh, and right downtown on Center Street.
Southside Steakhouse
170 S Main St, Rutland
My dinner pick, and one of my date night answers too. Steaks on South Main Street.
Ramunto's Sicilian Pizza
102 Strongs Ave, Rutland
My pizza answer in Rutland. Sicilian style pies on Strongs Ave.
Toad's Burger Bar
25 Main St, Poultney
The burger worth driving to Poultney for. Smash burgers on Main Street.
The Mad Rose
42 Center St, Rutland
My pick for a drink downtown. Craft cocktails and mocktails, plus small plates, on Center Street.
Michelle's Sweet Creations
73 Main St, Fair Haven
My sweet tooth answer. Cakes, cupcakes, and baked treats on Main Street in Fair Haven.
Date Night
Roots the Restaurant
55 Washington St, Rutland
Date night dinner, option one. Local, seasonal cooking on Washington Street.
Treviso Vermont
24 Wales St, Rutland
Date night dinner, option two. Italian on Wales Street.
Also Good
Or Southside Steakhouse, my dinner pick above. All three work.
Paramount Theatre
30 Center St, Rutland
After dinner, a show at the Paramount. The restored 1913 theatre on Center Street hosts concerts, comedy, and touring shows. Or skip the show and just walk around downtown.
Shopping
Downtown stops and a barn worth the short drive.
Max + Dot
Center St, Rutland
Women's boutique on Center Street with activewear, leisurewear, and casual pieces. One of my regular downtown stops.
Loose Loona
11 Center St, Rutland
Tea house and gift shop on Center Street. Scandinavian inspired, calm, and also my rainy day hiding spot with a warm drink.
GreenSpell Plant Shop
35 Center St, Rutland
Houseplants, pots, care supplies, and genuinely helpful plant advice on Center Street.
The Sparkle Barn
1509 US-7, Wallingford
Gift shop and art gallery in a big colorful barn on Route 7 in Wallingford. Handmade gifts, an upstairs Bloom Room, and a Magic Garden out back. You will not leave empty handed.
Books
Two bookstores I make time for, plus the rainy day plan.
Phoenix Books
2 Center St, Rutland
Our indie bookstore on Center Street in Rutland. Staff picks, author events, and my favorite place to browse before a show at the Paramount.
Northshire Bookstore
4869 Main St, Manchester Center
Huge. It has a little coffee shop inside and it is just fun. It is up in Manchester, so it is a drive, but I make it anyway.
Rainy Day
Rainy day plan: a local coffee shop or Loose Loona, a warm drink, and a good book. That is it. That is the whole plan.
Outdoors & Water
A gorge, a lake, and two downtown walks.
Clarendon Gorge
Clarendon
Not really a hike. It is a short walk from the parking area down to the Mill River, with a beachy spot by the water and a suspension bridge. My favorite quick reset, and a great swimming hole in summer.
Lake Bomoseen
Bomoseen State Park, 22 Cedar Mountain Rd, Castleton
Our summer lake. It is the largest lake entirely in Vermont, and Bomoseen State Park has a sandy beach, boat rentals, and room to spread out.
Walk Downtown Rutland
Downtown Rutland
Walking downtown Rutland is its own activity. Center Street, Merchants Row, the murals and sculptures, coffee in hand.
Walk Downtown Fair Haven
Downtown Fair Haven
Same goes for downtown Fair Haven. A slow loop, a stop at Michelle's, and nowhere to be.
With the Kids
Easy yeses for a family afternoon in Rutland.
Wonderfeet Kids Museum
66 Merchants Row, Rutland
Hands on everything. A kid sized diner, farmers market, train, and art room on Merchants Row. My kids can burn hours here.
Amazing Glaze Pottery
25 Center St, Rutland
Pottery painting on Center Street. Pick a piece and paint it your way. An easy yes for a weekend afternoon.
Self Care
Hair and nails, the two I actually book.
Seasonal
The market, creemees, fall roads, and winter tubing.
Vermont Farmers Market
Depot Park, Rutland (May to Oct) and 251 West St, Rutland (Nov to Apr)
The Rutland market. Outdoors at Depot Park from May to October, then it moves indoors at the Vermont Farmers Food Center on West Street for winter. Fresh produce, baked goods, maple, and live music on Saturdays.
Stewart's Shops
Several locations around Rutland
My creemee answer, and I am not picky about which one. I like all the Stewart's shops, to be honest. There are several around Rutland, so there is always one on the way.
Fall
Fall: driving the back roads. No destination, windows down, foliage up. That is the whole recommendation.
Killington Tubing Park
Killington Resort, 4763 Killington Rd, Killington
Full disclosure: I do not ski or snowboard. For a Vermonter that is basically a cardinal sin. My winter move is tubing at Killington, lift served lanes, no skill required, and playing in the yard with the kids making snowmen.
Worth the Drive
Outside the usual loop, still on my list.
The Cookster
1 Lamere Sq, Ludlow
Quick lunch, awesome food to go, always high quality, and always something I like. The menu changes, so check their Facebook before you go.
Also Worth It
Also worth the drive: Northshire Bookstore and Stella's Salon Plus, both in Manchester, listed above.
One Perfect Day
If you only have one day, do it like this.
Daytime
Daytime: start at Clarendon Gorge for a short walk and, in summer, a swim. Or make it a Lake Bomoseen beach day.
Evening
Evening: head to downtown Rutland. Browse Phoenix Books and the Center Street shops, grab dinner at Roots, Treviso, or Southside, then a show at the Paramount.