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Road Trip Ideas

Scenic Routes & Road Trip Adventures

If you love a good drive, whether you’re on a Harley, in a Jeep, or behind the wheel of anything that makes you smile, you’re in the right place. Our family happens to be fully aboard the Harley‑Davidson and Jeep bandwagons, so naturally, we’ve created a bunch of fun road trip itineraries. When you book a stay with us, we are happy to share some scenic route itineraries if you are interested.

Consider this a little corner of the internet where we share our favorite scenic routes, hidden gems, and “you’ve‑got‑to‑try‑this” detours. These drives are perfect for riders, off‑road wanderers, weekend explorers, and anyone who believes the best stories start with a full tank and an open road.

While we’re busy drafting the map routes Mom has programmed into the Harley, or sketched out on the atlas, we’ve are also rounding up a handful of great road‑trip articles from around the web. You might find them interesting too. Enjoy the finds.

Scenic Drives & Motorcycle/Jeep Routes 🌸☀️🍂

Route 100
- Quintessential Vermont drive -- lucky for us, Pine Ridge is located on scenic VT Route 100!
- Runs north-south through the entire state of Vermont
- This is the iconic Vermont foliage route
- Expect rolling farmland, covered bridges, and fiery maple canopies.
Route 17 – Appalachian Gap
- ~40 miles with 53 turns in just 7 miles near the Appalachian Gap.
- This route offers a thrilling ride and dramatic elevation changes with sweeping views of Camel’s Hump State Forest
- Best for experienced motorcyclists and adrenaline-seeking drivers
Molly Stark Byway (Route 9)
- ~40 miles (Bennington to Brattleboro)
- Named after the wife of Revolutionary War hero General John Stark, this southern Vermont route is rich in history and color
- Expect mountain vistas, quaint villages, and scenic overlooks
- Best for history buffs, fall photographers, and relaxed riders
Mad River Loop (VT-17, 116, 100, 125)
- ~66 miles - loop through the Mad River Valley with a mix of technical curves and peaceful farmland
- Great for a half-day ride or drive with plenty of scenic stops
- Best for motorcyclists and foliage chasers looking for variety
Lake Champlain Byway
- ~81 miles - a lakeside route with views of the Adirondacks and Green Mountains
- Best enjoyed in early to mid-October when the colors reflect off the water
- Best for long weekend drives and relaxed motorcycle cruising

Reminder: Pine Ridge has a shed out back, which is perfect for parking your motorcycle!

Planning a day along VT Route 100? Here’s how we’d spend it:

Morning, coffee at Pine Ridge, then a short drive south to Weston to the original Vermont Country Store (open since 1946)
Midday, backtrack north and turn onto Route 100A for Plymouth Notch to Calvin Coolidge’s birthplace (and check out the Plymouth Cheese Factory)
Stop at Long Trail Brewery near Bridgewater Corners in the afternoon for a drink along the river before heading back for dinner

Want a custom version? Book a stay with us!

Vermont Explored: The 10 Most Beautiful Road Trips in Vermont: Must-Visit Scenic Byways

Vermont Explored: Take a Stunning Route 100 Vermont Fall Foliage Road Trip
Did you know Pine Ridge is located on VT scenic Route 100!?!

Tour VT via the Vermont Creemee Ice Cream Trail
- Find a Location: Use the Creemee Locator to find the best local creemee spots tucked away in Vermont's valleys and farm towns
- Get a Stamp: Present your passport at the window and collect a unique stamp from each location you visit
- Enjoy a Treat: Pick your favorite flavor, sit back, and enjoy!
Some local spots on the Creemee Trail include:
- Green Mountain Sugar House, Ludlow, VT *** Right up the street from Pine Ridge (6 minutes)🍦
- Vermont Country Store, Weston, VT
- Abracadabra Coffee Co, Woodstock, VT
- Farmer and the Bell, Woodstock, VT
- Green Mountain Gumbo, Woodstock, VT
- White Cottage Snack Bar, Woodstock, VT
- Woodstock Scoops, Woodstock, VT
- Sunrise Farm, White River Junction, VT

Covered Bridges ❄️🌸☀️🍂

Calvin Coolidge Bridge (Plymouth, ~7 minutes)
A small but scenic bridge near the Calvin Coolidge Historic Site. Perfect for a quick photo stop while exploring the village
Taftsville Covered Bridge (Woodstock, ~33 minutes)
One of Vermont’s oldest and most iconic bridges, painted bright red and spanning the Ottauquechee River. A favorite for photographers
Quechee Covered Bridge (Quechee, ~35 minutes)
In the heart of Quechee Village, this bridge offers views of the gorge and easy access to shops and restaurants

Distances noted above are from Pine Ridge to each destination

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