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Middlebury & Otter Creek Valley Bike Tour

  • Middlebury with falls on Otter Creek
  • Green Mountains from valley near Middlebury
  • Brandon Gap in fall
  • Deer in woods
  • Discovery bike in meadow
  • Middlebury Gap
  • Apple on tree
  • Jersey cow through fence
  • Trilium, fiddlehead ferns, wild ginger: Vermont flowers
DURATION
6 Day(s)
DAILY BIKING
13 to 43 miles
TRIP DIFFICULTY
2-Easier to Intermediate
STARTING FROM
$2295
SINGLES ADD FROM
$450

Trip Overview

For quiet Vermont roads, historic buildings, delicious food and peaceful scenery, this tour can’t be beat. Meet in the quaint old town of Brandon, where you spend two nights — and enjoy strolling by the picturesque buildings and shops. Then hop on your bicycle and explore serene farm and forest landscapes of the surrounding valley. Or for more of a challenge, take the option to add climbs through two famous Vermont passes, known as “gaps.”

Head to Middlebury for three nights to enjoy this college town and all its glory. Walk along the village green and hear the rush of the falls on Otter Creek. Browse the antique shops and galleries. The brick and stone buildings make you feel as if you’re stepping back in time. Robert Frost taught at the college here and lived nearby, where he wrote many of his famous poems.

Sample fresh foodie delights and visit local craft breweries as you cycle through the rolling terrain between Lake Champlain and the Green Mountains. Tour a fascinating marble works — source of stone in many well-known structures. Don’t miss the chance to stop at a local pottery studio, munch on treats from farm stands, and meet furry friends at an alpaca or a Morgan horse farm. And for more miles, take the option to ride to the shores of Lake Champlain. You experience some of Vermont’s best scenery, history and cycling routes on our Middlebury & Otter Creek Valley tour.

See a list of all current Vermont tours

Itinerary

From start to finish, check out the route.

DAY 1 - Arrival Day
Distance: 13.5 miles |Terrain: Easier | Brandon Inn
Meet at the Brandon Inn in Brandon, Vermont, for a 2 p.m. warmup ride north to Leicester and back. Enjoy quiet roads as you get a feel for your bike. If time allows, stop in the quaint town of Leicester — featuring a meeting house built in 1826. Gather for a welcome dinner at Café Provence.
DAY 2 - Marble Works & Gap Option
Distance : 27, 35 or 43 miles | Terrain: Easier with Advanced Option | Brandon Inn
After a country breakfast at the inn, your main route is to cycle to the Marble Museum in Proctor and return via Pittsford. Enjoy four covered bridges along the way. The Vermont Marble Museum (entrance fee included) and gift shop are well worth a visit. Vermont marble was used to construct many famous buildings, like the Lincoln Memorial in Washington, D.C. A picnic lunch is included. You also have the option to challenge your legs with a loop through the advanced terrain of Brandon Gap either before breakfast or in the afternoon after returning from the standard ride. Another shorter option is to cycle to the grand Wilson Castle (entrance fee on your own, or just admire it from the outside). This stately building was constructed starting in 1885 and has an intriguing mix of Dutch Neo-Renaissance, Scottish baronial, Queen Anne, and Romanesque Revival architecture. Dinner with the group is at the inn tonight.
DAY 3 - To Middlebury & Lana Falls Hike
Distance: 21 or 40 miles | Terrain: Easier to Intermediate with Advanced Option | Middlebury Inn
Cycle to Middlebury via Branbury State Park with an option to do a 1-mile loop hike to the beautiful Falls of Lana with views of Lake Dunmore. The longer cycling option includes an advanced climb through Middlebury Gap. Lunch is on your own. Cycle into Middlebury — a cyclist’s paradise with shops, cafes, bakeries, breweries and the well-known college by the same name. Dinner is at the inn.
DAY 4 - Bristol and Farm Stand
Distance: 33 miles | Terrain: Easier to Intermediate | Middlebury Inn
Today’s route meanders through valley farmland to the town of Bristol, chartered in 1762. Bristol has a mix of classic old-time architecture with an haute foodie experience making it an ideal lunch stop. Try the Bobcat Café and Brewery or Snap’s Restaurant on Main Street. The Bristol Cliffs Café has great coffee and a portobello panini or chicken burrito. Top it off with a kale salad or something from their pastry shelf. Shops in town include a bookstore and gift shops. If you crave soft-serve ice cream (try the maple!), don’t miss the Village Creeme Stand. There’s an option to visit one of the state’s best potters whose customers included George Harrison, the late and great member of The Beatles. On your return to Middlebury, pass an apiary/organic farm with a farm stand. If you get back to Middlebury early, check out the shops in town or take a tasting tour of the various spirits, beer, and winery options — as well as sample the best coffee roasted in the state at Vermont Coffee Company’s café. You are on your own for dinner tonight.
DAY 5 - Vergennes & Kingsland Bay
Distance: 22 or 39 miles | Terrain: Easier to Intermediate | Middlebury Inn
Today’s shorter option is to cycle up to Vergennes and back. Vergennes bills itself as Vermont’s smallest city. It was the state’s first city, incorporated in 1788. Old buildings abound: the 1897 City Hall and Opera House are centerpieces of this town with a two-block-long main street that bustles with shops and great cafés. The longer option incorporates a loop to beautiful Kingsland Bay, which offers views out to Lake Champlain. For those wanting to explore more of what Middlebury has to offer by way of shops and sites, this would be the afternoon to do it. Our final celebration dinner is together at the Middlebury Inn.
DAY 6 - Departure Day
Distance: 22 or 39 miles | Terrain: Easier to Intermediate
Enjoy returning to Brandon via farm country. Pass the beautiful Shard Villa, which is on the National Register of Historic Places. Then wind your way into town alongside Otter Creek. You can grab a quick shower at the inn before saying farewell. Lunch is on your own.

Map

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

Start End Cost Availability

What’s Included

5 nights’ lodging, 5 breakfasts, 1 picnic lunch, 4 dinners (you are on your own for dinner 1 night in Middlebury), van support, 1 free transit time each way (start and end) between Burlington Airport and Brandon Inn, maps and direction and/or phone app-based navigation if desired, two experienced leaders, use of a bicycle and helmet, water bottle to keep, T-shirt, admission to marble museum. Airfare not included.

Dates & Pricing

Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $500 holds your reservation for most tours. For weekend tours, the deposit is $300.

What’s Included

5 nights’ lodging, 5 breakfasts, 1 picnic lunch, 4 dinners (you are on your own for dinner 1 night in Middlebury), van support, 1 free transit time each way (start and end) between Burlington Airport and Brandon Inn, maps and direction and/or phone app-based navigation if desired, two experienced leaders, use of a bicycle and helmet, water bottle to keep, T-shirt, admission to marble museum. Airfare not included.

Inns

Where you stay along the way.

Brandon Inn
The family-owned Brandon Inn located in the heart of Vermont has a relaxed and friendly atmosphere. The innkeepers strive to deliver the highest standard of comfort and amenities to their guests. The inn also retains a unique charm and feeling of history, an increasingly difficult feature to find in the modern world. Enjoy this ideal location situated opposite the village green and bandstand in the center of the village.
Middlebury Inn
The Middlebury Inn is a delightful destination where guests can enjoy historic hospitality, and walk, bike, or drive to their favorite attraction then return to the relaxing comfort of our inn. It's considered one of the five oldest inns in America.

Residing in the heart of the Champlain Valley, the Middlebury Inn has been welcoming guests since 1827. Overlooking the village greens of this Vermont shire town, this historic inn has elegantly restored guest rooms with formal Victorian accents.

Gallery

Images from this tour. Click each to see it larger.

Middlebury with falls on Otter Creek Green Mountains from valley near Middlebury Brandon Gap in fall Deer in woods Discovery bike in meadow Middlebury Gap Apple on tree Jersey cow through fence Trilium, fiddlehead ferns, wild ginger: Vermont flowers