Road Trips Let us know where you've been on your Harley, the best places to visit on a bike, etc.

What say you?

Thread Tools
 
Search this Thread
 
Old Sep 1, 2024 | 12:47 PM
  #1  
kojak's Avatar
kojak
Thread Starter
|
Seasoned HDF Member
15 Year Member
Community Builder
Liked
Loved
Joined: Jan 2007
Posts: 5,624
Likes: 4,077
From: Virginia
Default What say you?

I’m retiring May 1st 2025. Gonna go on a 4-6 week solo trip from Winchester Va starting May15th.
Only destinations planned are Key West in the beginning and Cape Breton on the return. Help plan my trip. I do need to stop in San Jose for family but rest is wide open.
 
Reply
Old Sep 1, 2024 | 03:00 PM
  #2  
deadhawg's Avatar
deadhawg
Stellar HDF Member
Veteran: Navy
15 Year Member
Liked
Community Favorite
Joined: Apr 2010
Posts: 2,960
Likes: 1,988
From: CA
Default

Originally Posted by kojak
I’m retiring May 1st 2025. Gonna go on a 4-6 week solo trip from Winchester Va starting May15th.
Only destinations planned are Key West in the beginning and Cape Breton on the return. Help plan my trip. I do need to stop in San Jose for family but rest is wide open.
So many good roads but six weeks (or six months) is not enough to ride them all. Since you're going to be in CA, there's a couple roads most would recommend, ride the PCH (Pacific Coast Highway, CA 1) from Cambria to Carmel then to San Jose. My choice from there would be to avoid San Francisco and ride east on 120 to Yosemite, Spend at least a couple days there, including the road to Glacier Point, then through Yosemite to 395 north then 89 to Lake Tahoe then on to Chester then 36 back to the coast and the PCH north from there.
 
Reply
Old Sep 1, 2024 | 06:54 PM
  #3  
Rocker NH's Avatar
Rocker NH
Grand HDF Member
Shutterbug
Liked
Loved
Community Favorite
Joined: Jul 2012
Posts: 3,909
Likes: 7,598
From: NH
Default

Originally Posted by kojak
I’m retiring May 1st 2025. Gonna go on a 4-6 week solo trip from Winchester Va starting May15th.
Only destinations planned are Key West in the beginning and Cape Breton on the return. Help plan my trip. I do need to stop in San Jose for family but rest is wide open.
You a couple days after you retire---Good Luck My man--I,m jealous

 
Reply
Old Sep 1, 2024 | 08:09 PM
  #4  
Cosmic Razorback's Avatar
Cosmic Razorback
Club Member
15 Year Member
Community Builder
Community Influencer
Active Streak: 30 Days
Joined: Aug 2008
Posts: 21,759
Likes: 22,951
From: North Carolina
Riders Club Member
Default

Congratulations, I planning to hang it up on March 31, 2025.

My only comment on Florida and Key West is get down there and out before June. I’ve spent a lot of time in Florida on two wheels and boating. Summer is no fun with the heat and the daily pop up showers. Isle Islamorada is a great place to stay. Easy one day ride to KW and back without being in the middle of all the crazy.

The Best KW trip we did on two wheels was in December. We rode down from I-I on Christmas Day to KW in a t-shirt.

Sounds like an awesome ride!
 
Reply
Old Sep 2, 2024 | 06:03 AM
  #5  
Geezr Glidr's Avatar
Geezr Glidr
Grand HDF Member
15 Year Member
Liked
Joined: Jun 2009
Posts: 3,520
Likes: 270
From: Wellsboro, PA
Default

Originally Posted by kojak
I’m retiring May 1st 2025. Gonna go on a 4-6 week solo trip from Winchester Va starting May15th.
Only destinations planned are Key West in the beginning and Cape Breton on the return. Help plan my trip. I do need to stop in San Jose for family but rest is wide open.
kojak, my only suggestion is WV & western NC. One of my favorites is 33 out of Harrisonburg, all the way to Seneca Rocks, but since you're in Winchester you've probably been on it a few times! Personally, I hate 81 and I avoid it like the plague. After you hit WV, pick a road & work your way over to Beckley & down 77. Then 81 to 26, and a few roads in NC. That's all I can offer! I love WV & western NC, and try to get there a couple times every summer from upstate PA.
 
Reply
Old Sep 2, 2024 | 06:33 AM
  #6  
NorthWestern's Avatar
NorthWestern
Club Member
10 Year Member
Loved
Community Favorite
Top Answer: 10
Joined: Apr 2016
Posts: 11,576
Likes: 8,405
From: Inland NW
Riders Club Member
Default

When you get to the left, go north young man! Across the border and go through Banff and Jasper on your way back to the NS
 
Reply
Old Sep 2, 2024 | 12:23 PM
  #7  
kojak's Avatar
kojak
Thread Starter
|
Seasoned HDF Member
15 Year Member
Community Builder
Liked
Loved
Joined: Jan 2007
Posts: 5,624
Likes: 4,077
From: Virginia
Default

Originally Posted by NorthWestern
When you get to the left, go north young man! Across the border and go through Banff and Jasper on your way back to the NS
Yup, I'm thinking the same way on the way back.
 
Reply
Old Sep 2, 2024 | 12:30 PM
  #8  
DK Custom's Avatar
DK Custom
Platinum Sponsor
15 Year Member
Liked
Loved
Community Favorite
Joined: Nov 2010
Posts: 18,685
Likes: 5,818
From: Hickory Flat, Mississippi
Default

Originally Posted by kojak
I’m retiring May 1st 2025. Gonna go on a 4-6 week solo trip from Winchester Va starting May15th.
Only destinations planned are Key West in the beginning and Cape Breton on the return. Help plan my trip. I do need to stop in San Jose for family but rest is wide open.
Congrats on your upcoming retirement.

We have a Ride Report Section on our website that you can see HERE. It has thousands of photos and comments of our riding around North America. Should give you some ideas of great places to visit.

Here are some of our top places we like to ride:

Beartooth Pass

Million Dollar Highway

Bryce Canyon

Zion National Park

Eureka Springs area

Smokey Mountains area

Coast of Cali, above San Jose

Black Hills area

There are many more, as seen in the link above, but these are some of our favorites.

Kevin
 
__________________
DKCustomProducts.com
Call/Text: 662-252-8828
Email: Support@DKCustomProducts.com
Open House Details














Reply
HD Forum Stories

The Best of Harley-Davidson for Lifelong Riders

story-0

7 Times Harley-Davidson Chucked Tradition Out the Window

 Verdad Gallardo
story-1

7 Surprising Harley-Davidson Products that Are Not Motorcycles

 Verdad Gallardo
story-2

8 Best Harley-Davidson Motorcycles Ever

 Pouria Savadkouei
story-3

10 Worst Harley-Davidson Motorcycles Ever

 Pouria Savadkouei
story-4

Killer Custom's Jail Break Is The Breakout That Refused to Blend In

 Verdad Gallardo
story-5

Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?

 Verdad Gallardo
story-6

Harley-Davidson Reveals Super Cool Cafe Racer Concept

 Verdad Gallardo
story-7

Engraved Rebellion: Inside Bundnerbike's Glam Rock II

 Verdad Gallardo
story-8

10 Motorcycles You Should Never Buy

 Joe Kucinski
story-9

10 Things Harley-Davidson Needs to Fix in 2026

 Verdad Gallardo
Old Sep 2, 2024 | 01:04 PM
  #9  
kojak's Avatar
kojak
Thread Starter
|
Seasoned HDF Member
15 Year Member
Community Builder
Liked
Loved
Joined: Jan 2007
Posts: 5,624
Likes: 4,077
From: Virginia
Default

Thanks Kevin. Ive ridden most of the areas in Colorado, Utah, S Dakota, Wyoming, Montana. i'm just trying to thread together a doable ride plan from Va to Key West to San Jose and back east to Cape Breton and then down to Va. Think of it as a 3 corners ride. Key West, San Jose, NS. I have little interest in riding in the south and south west outside of making the trek to Key West. From FL, I will probably start a NW trek to the west coast and I like the idea of going up to Vancouver and riding back east through Jasper/Banff.
 
Reply
Old Sep 2, 2024 | 06:08 PM
  #10  
Grandslam's Avatar
Grandslam
Road Warrior
10 Year Member
Liked
Loved
Community Favorite
Joined: Aug 2011
Posts: 1,314
Likes: 376
From: Mississippi
Default

Congratulations on your retirement. As mentioned, you need to get KW and the south out of the way EARLY on. Safe travels.
 
Reply



All times are GMT -5. The time now is 01:43 PM.

story-0
7 Times Harley-Davidson Chucked Tradition Out the Window

Slideshow: Harley-Davidson built its reputation on nostalgia, but every so often, the company took a hard left turn into the future.

By Verdad Gallardo | 2026-05-20 11:18:19


VIEW MORE
story-1
7 Surprising Harley-Davidson Products that Are Not Motorcycles

Slideshow: The bar-and-shield logo shows up on far more than motorcycles, some of the company's most unexpected products have nothing to do with riding.

By Verdad Gallardo | 2026-04-29 16:50:35


VIEW MORE
story-2
8 Best Harley-Davidson Motorcycles Ever

Slideshow: Not every Harley gets it right, but these are the ones that genuinely earned their reputation.

By Pouria Savadkouei | 2026-04-15 14:23:21


VIEW MORE
story-3
10 Worst Harley-Davidson Motorcycles Ever

Slideshow: From the troubled AMF years to modern misfires, these bikes earned reputations for reliability issues, questionable engineering, or disappointing performance.

By Pouria Savadkouei | 2026-04-01 20:01:09


VIEW MORE
story-4
Killer Custom's Jail Break Is The Breakout That Refused to Blend In

Slideshow: Killer Custom's "Jail Breaker" build focuses more on stance and visual aggression than mechanical overhaul.

By Verdad Gallardo | 2026-03-18 19:20:32


VIEW MORE
story-5
Crazy Bunderbike Build Looks Amazing, But Is It Impossible to Ride?

Slideshow: The Swiss custom shop has taken a Harley Softail and stretched it into something so long and low that it looks closer to a rolling sculpture than a conventional motorcycle.

By Verdad Gallardo | 2026-03-07 16:15:30


VIEW MORE
story-6
Harley-Davidson Reveals Super Cool Cafe Racer Concept

Slideshow: Harley-Davidson's new RMCR concept revives the café racer formula with modern hardware-and it may be exactly the reset the company needs.

By Verdad Gallardo | 2026-03-04 12:23:37


VIEW MORE
story-7
Engraved Rebellion: Inside Bundnerbike's Glam Rock II

Slideshow: A standard cruiser becomes an intricate metal canvas in the hands of a Swiss custom house known for pushing Harley-Davidson platforms far beyond their factory brief.

By Verdad Gallardo | 2026-02-24 18:19:44


VIEW MORE
story-8
10 Motorcycles You Should Never Buy

Slideshow: There is no shortage of great motorcycles to buy, but we would avoid these ten.

By Joe Kucinski | 2026-02-19 14:50:51


VIEW MORE
story-9
10 Things Harley-Davidson Needs to Fix in 2026

Slideshow: Harley-Davidson's challenges aren't abstract; they show up in dropping shipments, shrinking dealer traffic, and strategic decisions that aren't yet translating into growth.

By Verdad Gallardo | 2026-01-13 18:33:17


VIEW MORE