Road trip from Portland to Winston-Salem
All Category
Outdoor Activities
Museums
Concerts & Shows
Food & Drink
Sights & Landmarks
Shopping
Fun & Games
Show more (4+)
All Category
Outdoor Activities
Museums
Concerts & Shows
Food & Drink
Sights & Landmarks
Shopping
Fun & Games
Nightlife
Nature & Parks
Classes & Workshops
Reset
Show less
ITINERARY
48h 30m2,748 miles26 stops
1
Sellwood
Neighborhood with a pleasant, small shopping area with dozens of antique shops.
2
South Waterfront Lower Tram Terminal
The Tram is a popular destination for tourists, locals and people just looking to try something fun. The lower tram terminal is at the intersection of South Moody Avenue & Gibbs Street --the most transportation-diverse intersection in the country. Besides one of the nation's only aerial commuter trams, you'll see cars, buses, a streetcar, a soaring pedestrian bridge, a cycle track and the densest bike parking in America's #1 biking city. Bike valet is offered free to the public at Portland Aerial Tram Monday through Friday. Exiting the upper terminal you'll see the largest enclosed sky bridge in North America. Take a right to access an outdoor patio with seating and views of the terminal, the cityscape, the Willamette River and, on a clear day, Mount Hood and Mount St Helens. The upper terminal links to the 4T Trail--a self-guided tour by train, trail, tram and trolley. Much of Marquam Hill is a natural area with several trails.
3
Section 37 Axe Room
4
Ann Morrison Park
5
Boise State University
Idaho's metropolitan college is located one mile from the downtown area.
6
Lucky Peak State Park
7
Great Salt Lake
This 20,000 square mile lake, the second saltiest in the world, is also a wildlife refuge attracting millions of migratory birds every year to the ten islands within it.
8
Red Butte Garden
Red Butte Garden is the largest botanical garden in the Intermountain West and, together with the University of Utah, is the state arboretum. The Garden has welcomed guests since 1985 and consists of over 21 acres of developed gardens and five miles of hiking trails winding through an extensive Natural Area. All just minutes away from downtown Salt Lake City. The Garden is renowned for plant collections, themed gardens, over 560,000 springtime blooms, gorgeous private rental spaces, a world-class summer concert series, and award-winning horticulture-based educational programs.
9
Sugar House Park
Once the site of Utah Territorial Prison, this park is a lot more pleasant today, with a gently rolling landscape great for running.
10
Cache La Poudre River
Colorado's only designated National Wild and Scenic River provides thrilling whitewater and paddling adventures.
11
Farm Fusion In The Kitchen
12
The Farm at Lee Martinez Park
13
Platte Valley Antique Mall
14
Martin Luther King, Jr "i Have A Dream" World Peace Rose Garden
15
Kaw River Rustics
16
Line Creek Trail
17
Howl at the Moon Kansas City
Howl at the Moon Kansas City is the hottest spot in the Power and Light District! Our high-energy dueling pianos and amazing events make us the coolest spot for Kansas City nightlife! From company functions to happy hour with friends to bachelorette parties in Kansas City, the party is always at Howl at the Moon come and see us.
18
Game Show Battle Rooms
You're IN the Game Show! Game Show Battle Rooms is one of the nation's only immersive game show experiences for everyone to enjoy. Face-off against your friends, family, or coworkers in our custom arenas playing classic game shows! All hosted by our entertaining and engaging hosts. Perfect for your next birthday party, friend or family outing, or your next corporate team-building event!
19
Willard Library
20
Lexington Brewing & Distilling Co.
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
21
Waveland State Historic Site
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
22
Fayette Mall
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
23
Iron Heart Winery
24
Grand 18-Winston-Salem
25
Lam Museum of Anthropology, Wake Forest University
Discover North Carolina's only museum dedicated to the study of global cultures. Explore stories of humanity, from ancient archaeological sites to the celebrations and struggles of today. Learn about peoples around the world through their everyday and ceremonial objects, and visual arts. Changing exhibits highlight the Museum's collections of nearly 30,000 archaeological and ethnographic artifacts from more than 350 cultures and 90 countries. Admission is free.
26
Salem Lake
Customize this Trip
OVERVIEW
1
Start:Sellwood
Portland, Oregon·
4.5
(98) review
Neighborhood with a pleasant, small shopping area with dozens of antique shops.
2
Start:South Waterfront Lower Tram Terminal
Portland, Oregon·
4.0
(993) review
The Tram is a popular destination for tourists, locals and people just looking to try something fun. The lower tram terminal is at the intersection of South Moody Avenue & Gibbs Street --the most transportation-diverse intersection in the country. Besides one of the nation's only aerial commuter trams, you'll see cars, buses, a streetcar, a soaring pedestrian bridge, a cycle track and the densest bike parking in America's #1 biking city. Bike valet is offered free to the public at Portland Aerial Tram Monday through Friday. Exiting the upper terminal you'll see the largest enclosed sky bridge in North America. Take a right to access an outdoor patio with seating and views of the terminal, the cityscape, the Willamette River and, on a clear day, Mount Hood and Mount St Helens. The upper terminal links to the 4T Trail--a self-guided tour by train, trail, tram and trolley. Much of Marquam Hill is a natural area with several trails.
3
Start:Section 37 Axe Room
Boise, Idaho·
4.5
(9) review
10535 W Overland Rd, Boise, ID 83709-1436
4
Start:Ann Morrison Park
Boise, Idaho·
4.5
(96) review
1000 S Americana Blvd near Capitol and Americana boulevards, Boise, ID 83702
5
Start:Boise State University
Boise, Idaho·
4.5
(91) review
Idaho's metropolitan college is located one mile from the downtown area.
6
Start:Lucky Peak State Park
Boise, Idaho·
4.5
(95) review
74 Arrowrock Rd, Boise, ID 83716-5050
7
Start:Great Salt Lake
Salt Lake City, Utah·
4.0
(987) review
This 20,000 square mile lake, the second saltiest in the world, is also a wildlife refuge attracting millions of migratory birds every year to the ten islands within it.
8
Start:Red Butte Garden
Salt Lake City, Utah·
4.5
(925) review
Red Butte Garden is the largest botanical garden in the Intermountain West and, together with the University of Utah, is the state arboretum. The Garden has welcomed guests since 1985 and consists of over 21 acres of developed gardens and five miles of hiking trails winding through an extensive Natural Area. All just minutes away from downtown Salt Lake City. The Garden is renowned for plant collections, themed gardens, over 560,000 springtime blooms, gorgeous private rental spaces, a world-class summer concert series, and award-winning horticulture-based educational programs.
9
Start:Sugar House Park
Salt Lake City, Utah·
4.5
(99) review
Once the site of Utah Territorial Prison, this park is a lot more pleasant today, with a gently rolling landscape great for running.
10
Start:Cache La Poudre River
Fort Collins, Colorado·
5.0
(427) review
Colorado's only designated National Wild and Scenic River provides thrilling whitewater and paddling adventures.
11
Start:Farm Fusion In The Kitchen
Fort Collins, Colorado·
(0) review
2627 Cattlemans Rd, Fort Collins, CO 80524-2023
12
Start:The Farm at Lee Martinez Park
Fort Collins, Colorado·
4.5
(93) review
600 N Sherwood St, Fort Collins, CO 80521-2061
13
Start:Platte Valley Antique Mall
Omaha, Nebraska·
4.5
(9) review
13017 238th St I-80 Exit 420, Omaha, NE 68366-2121
14
Start:Martin Luther King, Jr "i Have A Dream" World Peace Rose Garden
Atlanta, Georgia·
4.0
(1) review
450 Auburn Ave NE, Atlanta, GA 30312-1504
15
Start:Kaw River Rustics
Topeka, Kansas·
4.5
(9) review
901 N Kansas Ave, Topeka, KS 66608-1212
16
Start:Line Creek Trail
Kansas City, Missouri·
5.0
(9) review
2699 NW 60th St, Kansas City, MO 64151
17
Start:Howl at the Moon Kansas City
Kansas City, Missouri·
4.5
(96) review
Howl at the Moon Kansas City is the hottest spot in the Power and Light District! Our high-energy dueling pianos and amazing events make us the coolest spot for Kansas City nightlife! From company functions to happy hour with friends to bachelorette parties in Kansas City, the party is always at Howl at the Moon come and see us.
18
Start:Game Show Battle Rooms
Overland Park, Kansas·
4.5
(9) review
You're IN the Game Show! Game Show Battle Rooms is one of the nation's only immersive game show experiences for everyone to enjoy. Face-off against your friends, family, or coworkers in our custom arenas playing classic game shows! All hosted by our entertaining and engaging hosts. Perfect for your next birthday party, friend or family outing, or your next corporate team-building event!
19
Start:Willard Library
Evansville, Indiana·
4.5
(97) review
21 N 1st Ave, Evansville, IN 47710-1294
20
Start:Lexington Brewing & Distilling Co.
Lexington, Kentucky·
4.5
(984) review
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
21
Start:Waveland State Historic Site
Lexington, Kentucky·
4.5
(97) review
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
22
Start:Fayette Mall
Lexington, Kentucky·
4.5
(91) review
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
23
Start:Iron Heart Winery
Allisonia, Virginia·
4.0
(7) review
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
24
Start:Grand 18-Winston-Salem
Winston Salem, North Carolina·
4.0
(72) review
5601 University Pkwy, Winston Salem, NC 27105-1313
25
Start:Lam Museum of Anthropology, Wake Forest University
Winston Salem, North Carolina·
4.0
(9) review
Discover North Carolina's only museum dedicated to the study of global cultures. Explore stories of humanity, from ancient archaeological sites to the celebrations and struggles of today. Learn about peoples around the world through their everyday and ceremonial objects, and visual arts. Changing exhibits highlight the Museum's collections of nearly 30,000 archaeological and ethnographic artifacts from more than 350 cultures and 90 countries. Admission is free.
26
Start:Salem Lake
Winston Salem, North Carolina·
4.5
(97) review
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
EXPLORE MORE
Discover Exciting Road Trip Inspirations
Portland to Las Vegas
970 miles
19h 12m
7 stops
Concerts & ShowsMuseumsSights & LandmarksFood & DrinkNature & Parks
Portland to Memphis
2,257 miles
39h 59m
32 stops
Sights & LandmarksConcerts & ShowsOutdoor ActivitiesMuseumsFun & Games
Portland to Louisville
2,320 miles
40h 33m
31 stops
Food & DrinkToursMuseumsFun & GamesShopping
Portland to Sacramento
581 miles
11h 14m
25 stops
Food & DrinkOutdoor ActivitiesNightlifeWater & Amusement ParksMuseums
Portland to Riverside
1,018 miles
19h 14m
29 stops
Outdoor ActivitiesMuseumsTraveler ResourcesNature & ParksFun & Games
Portland to San Jose
668 miles
12h 56m
30 stops
Sights & LandmarksOutdoor ActivitiesToursNature & ParksFood & Drink
EXPLORE OTHER
Check Out Different Road Trip Options
Greenville to Roanoke
290 miles
5h 38m
24 stops
MuseumsOutdoor ActivitiesShoppingFood & DrinkSights & Landmarks
Birmingham to Spring Valley
1,818 miles
31h 52m
19 stops
MuseumsSights & LandmarksNature & ParksTraveler ResourcesFun & Games
Washington to Sioux Falls
1,275 miles
23h 42m
23 stops
Concerts & ShowsFood & DrinkSights & LandmarksNature & ParksTours
Detroit to Yonkers
629 miles
11h 46m
28 stops
Nature & ParksFun & GamesToursConcerts & ShowsNightlife
Akron to Port Arthur
1,220 miles
23h 28m
27 stops
Nature & ParksTraveler ResourcesMuseumsFood & DrinkSights & Landmarks
Greenville to Kalamazoo
684 miles
13h 45m
21 stops
Outdoor ActivitiesShoppingSights & LandmarksNightlifeNature & Parks
FAQ
Frequently Asked Questions
What's the driving distance between Portland and Winston-Salem?
The distance is 2,748 miles
What's the travel time between Portland and Winston-Salem?
The driving time can vary depending on traffic conditions, but it is typically 48h 30m mins in normal traffic
What are some of the best cities to visit between Portland and Winston-Salem?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Winston-Salem?
There are plenty! Here are some stops you shouldn’t miss on your way to Winston-Salem
What’s the weather like in Winston-Salem?
The weather in Winston-Salem is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Winston-Salem in January
Weather in Winston-Salem in February
Weather in Winston-Salem in March
Weather in Winston-Salem in April
Weather in Winston-Salem in May
Weather in Winston-Salem in June
Weather in Winston-Salem in July
Weather in Winston-Salem in August
Weather in Winston-Salem in September
Weather in Winston-Salem in October
Weather in Winston-Salem in November
Weather in Winston-Salem in December
Interested in a detailed plan for your time in Winston-Salem?
Plan your dream Winston-Salem trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Winston-Salem
A 2-day itinerary in Winston-Salem
A 3-day itinerary in Winston-Salem
A 4-day itinerary in Winston-Salem
A 5-day itinerary in Winston-Salem
A 6-day itinerary in Winston-Salem
Where else can I travel to if I'm starting my trip in Portland?
We have a lot of great trip options for Portland! See the links below for all the itineraries we created for you