Fall Road Trip Itinerary: Colorado

Three Fall Road Trips Across America

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I’m a really, really seasonal person. The season’s affect me (in all good ways!) and I absolutely LOVE embracing them. Last year, I came to the conclusion that fall is my favorite season. Now, truth be told, I waver on this a lot but I get so excited about fall flavors, fall foliage, and fall fashion that I can hardly stand it. Since I am getting married in October, I will have one more major reason to love the season! As you may have heard, Edwin and I moved across the country to the East Coast but our move is most likely just temporary. I want to take full advantage of the East Coast while I live on it so I told Edwin that above all else, I want to go on a fall foliage road trip somewhere on this coast while we live over here. We are currently stuck between doing New England and the Blue Ridge Mountain Trail so stay tuned (p.s. my fingers are seriously crossed that this little trip will even happen at all!). My heart will always hold Colorado as a special place since I went to collage there (go Buffs!) so I’m looping Colorado in since their fall leaves are truly spectacular. So, without further ado, I give you three fall road trips across America: the Blue Ridge Mountain Trail, New England, and Colorado.

Three Fall Road Trips Across America

 Fall Road Trip Itinerary: Blue Ridge Mountain Trail

One: Blue Ridge Mountain Trail / 3 nights, 4 days

Day 1: Roanoke, VA to Woolwine, VA / Night 1 (Friday) in Woolwine at The Mountain Rose Inn 

In Roanoke, visit The Taubman Museum of Art for contemporary, colorful, and folksy art

Hop in your car and turn south on the Blue Ridge Parkway

Stop at Smart View Overlook & see the Trail Cabin

Continue south to Woolwine & check into a beautiful old Victorian home that has since been converted into a hotel, The Mountain Rose Inn

Jump back in the car to visit one of Virginia’s oldest wineries, Chateau Morrisette, for wine tasting & dinner (make a reservation ahead of time)

Head out for some bluegrass music to Floyd Country Store, which gets converted into a dance hall every Friday for the Friday Night Jamboree


Day 2: Woolwine, VA to Blowing Rock, NC / Night 2 (Saturday) at Blowing Rock Brewing Company Ale House & Inn

Enjoy a multi-course breakfast at Mountain Rose Inn

Checkout from Mountain Rose Inn in Woolwine & jump back on the Blue Ridge Parkway heading south

Make your first stop at Mabry Mill to take in the historic old millhouse property & gift shop (p.s. it’s one of the most photographed places along the Blue Ridge Mountain Trail)

Get back on the Parkway and head to the Blue Ridge Music Center (be sure to stop for photos along the way!) for a free Mid-Day Mountain Music Concert at noon and to tour the museum’s antique instrument displays

Pile back in the car and head to Blowing Rock, NC

Option to take a detour to stop to buy apples at The Orchard at Altapass

Pop into Harvest Farm in Valle Crucis for pumpkins, winter squash, and gourds

Arrive in Blowing Rock & check into Blowing Rock Brewing Company Ale House & Inn (another lodging option is The Mast Farm Inn)

Shop along Main Street in Blowing Rock to see the local antique shops and galleries

Enjoy a local beer on the lawn at Blowing Rock Brewing Company Ale House & Inn

Drive to a dinner of Appalachian comfort food in an old house at Over Yonder (10 miles over yonder (pun intended) in Valle Crucis, make a reservation ahead of time)


Day 3: Blowing Rock, NC to Ashville NC / Night 3 (Sunday) at Sourwood Inn

 Grab a quick breakfast in town before hitting the road

Veer off of the Parkway to drive to the top of Grandfather Mountain to see the Mile High Swinging Bridge

Stop off the Parkway to do mile hike up to Linville Falls

Drive to lunch at Knife & Fork in Spruce Pine, NC for locally sourced Appalachian food

Hop back on the Parkway & head to the Sourwood Inn

Option to stop at Mount Mitchell State Park for hike to a viewing platform & Craggy Gardens to see mountaintops + thickets of rhododendron and mountain laurel

Check into the craftsman-style inn, Sourwood Inn (less than 30 minutes outside of Asheville)

Head to Asheville for drinks at Sovereign Remedies & dinner at Gan Shan Station 


Day 4: Ashville, NC to Home

Breakfast in Asheville

Tour the Biltmore Estate

Lunch + beer tasting in town at Wicked Weed Brewery

Shop around Asheville

Book shop & sip wine + champagne at the Battery Park Book Exchange & Champagne Bar

Dinner at The Admiral

Go to sleep and drive home in the morning


Fall Road Trip Itinerary: New England

Two: New England / 5 Night, 6 Days

Day 1: Boston, MA / Night 1 at The Verb Hotel

Check into the Verb Hotel for laid-back, music-forward vibes

Either walk around Harvard & get drinks at Little Donkey for a more casual vibe or visit Yvonne’s for a more upscale drinks atmosphere

Dinner at local Italian favorite Grotto for some delicious fall flavors


Day 2: Boston, MA / Night 2 at The Verb Hotel

Breakfast at Tatte Bakery (Beacon Hill location)

Walk around Beacon Hill Neighborhood & look for cute doorknockers (particularly on Acorn and Chesnutt Streets)

Shop around Beacon Hill at Good for gifts, Crush for women’s clothing, Holiday for women’s clothing, Dress for purses & more, and December Thieves for accessories

Lunch at Boston Public Market

Pick a Boston activity for the afternoon… options: walking tour of Freedom Trail (free), admire the Boston Public Library, Visit Isabella Gardner Stewart Art Museum, walk through Boston Common & Boston Public Garden, and/or Shop up & down Newbury Street

Dinner at either Rosebud Kitchen for comfort food + craft cocktails, Myers and Chang for family-style Asian small plates, Sarma for modern Mediterranean, Border Café for tex-mdx + cajun cooking, Douzo for trendy sushi, or Loco for bata-style tacos + oysters


Day 3: Boston, MA to Woodstock, VT / Night 3 at Woodstock Inn & Resort

Grab coffee at The Thinking Cup & hop in your car to drive to Woodstock, VT

On drive from Boston to Woodstock, option to stop at Dartmouth College in Hanover, NH or in Deerfield, MA to tour historic homes

Check into The Woodstock Inn & Resort

Afternoon visit to Sugarbush Farm

Stop by the Woodstock Middle Bridge for a very photo-worthy destination

Walk around Woodstock picturesque town

Dinner at Woodstock Inn & Resort


Day 4: Woodstock, VT to Warren, VT / Night 4 at Pitcher Inn

Breakfast in town

Mosey around the historic town of Woodstock

Jump in the car and drive to Warren, VT

Check into The Pitcher Inn

Take an afternoon drive down the road to visit Blueberry Lake with canoes provided by the Pitcher Inn

Dinner at The Pitcher Inn


Day 5: Warren, VT / night 5 at Pitcher Inn

Breakfast at Pitcher Inn

Take a day excursion to Shelburne, VT

On the drive to Shelburne, option to stop at Camel’s Hump Alpaca Farm, VT

Arrive in Shelburne and visit Shelburne Farms, Shelburne Orchards (prepare to apple pick!), and Lake Champlain

On drive home from Shelburne, drive the Lincoln Gap mountain pass for gorgeous views and fall foliage as far as the eye can see


Day 6: Warren, VT to Home


Fall Road Trip Itinerary: Colorado

Three: Colorado / 5 Nights, 6 days

Day 1: Boulder, CO / Night 1 at The St. Julien Hotel

Check into the St. Julien Hotel on a Friday evening

Outdoor evening drinks + live music at the St. Julien

Walk to Pearl Street & watch the Pearl Street Stampede

Dinner at The Kitchen

Late Night drinks at the Bohemian Biergarten


Day 2: Boulder, CO / Night 2 at The St. Julien Hotel

Brunch at Brasserie Ten Ten

Shop on Pearl Street (especially the store Weekends)

Tailgate on The Hill or on Campus

Attend a CU Buffs football game (go Buffs!)

Dinner on the roof at West End Tavern for delicious bbq


Day 3: Boulder, CO to Vail, CO / Night 3 at the Sonnenalp Hotel

Morning like of The Flatirons (bring your camera for gorgeous views!)

Brunch at Lucile’s

Drive to Vail, CO

Check into the classic Vail hotel, Sonnenalp Hotel

Mountainside drinks at Garfinkel’s

Dinner at Sweet Basil for New American eats & a buzzy bar


Day 4: Vail, CO / Night 4 at the Sonnenalp Hotel

Breakfast in Vail Village

Shop in the village at Perch for women’s clothing, Skipper & Scout for children’s clothing, and Grey Salt for men’s clothing

Lunch at Mountain Standard for tavern-style fare, beers, and bourbon

Afternoon horseback ride at Beaver Creek Stables (only through September) or hike either Berry Picker (ride the gondola down) or Booth Falls (really gorgeous waterfall!)

Take the gondola up to Game Creek for dinner

Boozy bowling at Bol


Day 5: Vail, CO to Aspen, CO / Night 5 at Hotel Jerome

Breakfast at Sticky Fingers Café in Minturn

Drive to Aspen

Check into the historic Aspen hotel, Hotel Jerome

Rent bikes in town and ride to Woody Creek Tavern for lunch

Shop around town

Dinner in town

Live music at the Belly Up (check the schedule ahead of time for your trip & buy tickets)


Day 6: Aspen, CO to home

Outdoor activity of early morning hike of either Smuggler Mountain or Maroon Bells (great if you have more time) or bike/walk the Rio Grande Trail

Breakfast or Lunch at Hickory House

Drive home


I hope I gave you a bit of fall wanderlust with today’s post! Happy travels campers! xx

Artwork: the adorable artwork in my itineraries is borrowed from my dear friend Jen Peters (also see her work here)!

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  1. As a Massachusetts native I say go the New England route, but I may be a bit biased! Either way, all of these look like great options to choose from!

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