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The Best Road Trips for Baby Boomers

Category: Adventurous retirement

July 14, 2014 — It’s summertime and that means it must be time to plan a road trip – either for now or in the fall when the weather cools and traffic subsides. We are pretty sure that most baby boomers have a few routes on their personal bucket lists. In this article we will list 12 of our personal favorites to help you consider the possibilities. We also invite our members to suggest their “bests” in the Comments section below. You can subscribe to our free weekly newsletter to get more retirement ideas like this.

Types of great highways
You don’t have to drive far to find a great road – just about everyone probably has a favorite highway in their own part of the country. One that is near us in Connecticut is Route 154 between Guilford and Stony Creek (which is a great place to have lunch or take a boat tour of the Thimble Islands).

We think there are several factors that can make for a great, scenic highway. Some roads we list here combine many of these reasons.
– Views of the water
– Breathtaking mountains
– Amazing natural features
– Beautiful vegetation, especially seasonal
– Historic houses and buildings
– Fun to drive

Some Great Road Trips
This list was compiled from our personal experience and from a review of other articles on the subject. It is highly subjective, and that’s why we invite you to suggest your own favorites! Don’t forget that you can multi-task while exploring these wonderful roads – use the occasion to visit some potential retirement towns and communities in the surrounding area. To find them, use our State Directories. For some of these roads we’ve provided a link to our review of a nearby community that you might find interesting.

View near Islamorada

Overseas Highway – Route 1 from Key Largo to Key West, FL. The first part of this highway from the FL mainland to Key Largo is boring. But from Key Largo through Islamorada to the terminus of Route 1 in Key West is incredibly beautiful. You’ll frequently be beside a turquoise sea. You will cross the 7 mile bridge. And you will be following the route blazed by Henry Flagler’s short-lived Florida East Coast Railroad to Key West. The movie “True Lies” has action scenes and a spectacular helicopter/car chase on this highway.

Pacific Highway – Route 1 – California, Oregon, and Washington. Just about anywhere from Santa Barbara to the Canadian border on this road will produce jaw-dropping scenery of the Pacific Ocean and coastal mountains. Although this highways has 123 official miles, Route 1 is much longer. Driving it you need to be alert for mudslides, sharp turns, and detours. The 17-Mile Drive (it is actually less than that) goes across California’s Monterey Peninsula from the Pacific Grove to Carmel, while passing by to the famous Pebble Beach golf community. North of San Francisco don’t miss Mendocino or Eureka.

US 12 going through Grand Staircase-Escalante

US 12 going through Grand Staircase-Escalante

Utah Route 12 – This, one of the most stunning roads in the world, runs from Capitol Reef National Park to Bryce Canyon National Park. The route goes for an 124 miles at significant altitudes (9000′) as goes through forested mountains to the amazing bald mountains in Boulder. That’s where you should have an amazing lunch or dinner at the Hells Backbone Grill. From there the road begins following a narrow ridge along the red canyons of Grand Staircase-Escalante and Bryce Canyon National Parks. Not too far from there is the growing retirement town of St. George, definitely worth a visit.

Kancamagus Highway – New Hampshire. This 34.5 mile scenic drive along New Hampshire’s Rt. 112 in Northern New Hampshire offers some of the best Fall Foliage viewing opportunities. It has been designated an American Scenic Byway. Campton is an interesting stop a bit south of this road.

The High Road, Scenic Byway – New Mexico . This road follows several routes as it runs between former Spanish colonies Santa Fe and Taos. A friend just took this road and loved it for the ancient Indian pueblos, deserts, wildflower meadows, and artists’ colonies.

Views in the Beartooths

Views in the Beartooths

Beartooth Highway – Montana and Wyoming. Charles Kuralt called this the most beautiful highway in America. U.S. 212 runs from the northern entrance of Yellowstone near Cooke City to Red Lodge, Montana through Absaroka-Beartooth National Wilderness. At one point the road is just a few feet under 11,000′. Your editor went hiking here last year and it is beautiful!

Delaware Water Gap, PA and NJ. Interstate 80 hits an impressive obstacle as it crosses from Pennsylvania to New Jersey – the Delaware Water Gap. It is hard to keep your eyes on the road as you confront the evidence of natural forces that constrict the Delaware River here.

Highway 2, Nebraska. This discontinuous highway has 2 segments. The western segment begins at the South Dakota border northwest of Crawford and ends southeast of Grand Island at an intersection with Interstate 80. The eastern segment begins in Lincoln and ends at the Iowa border at Nebraska City. Along its more than 200 miles it features dramatic sandhills, remote countryside, expansive farmland, marshes and wetlands, winding rivers.

Loop Road, Acadia National Park – Maine. Thanks to the Rockefeller family this beautiful National Park is protected and easily enjoyed. See the views from the top of Mount Desert Island to stunning Bar Harbor below. Like most of the roads listed here, this 27-mile, two-lane artery is much less crowded in the off-season.

Cape Cod National Seashore

Cape Code National Seashore

Route 6 – Cape Cod, Mass. Allocate some time to explore this charming 117-mile route that wends through Cape Cod. You will go through forests, past saltbox homes in colonial villages, tidal ponds, and eventually end up at the Provincetown harbor. Don’t miss the towering sand dunes and beaches. Be sure to eat at the Lobster Pot in Provincetown.

Going to the Sun Road – Montana. Almost every list of the most scenic roads in America includes this drive that goes through Glacier National Park. You’ll see mountain peaks, snow, and follow the Continental Divide in the Rockies. Beautiful Whitefish isn’t on this road, but is definitely worth a detour.

Tail of the Dragon – Tennessee/North Carolina. Like we said, there are all kinds of reasons to pick a great road. This one is famous for its degree of difficulty and road excitement The official road is just 11 miles. People who love to drive come here to experience the sharp curves and thrills in their motorcycles and sports cars. The advice is not to come for the scenery (which must be nice) – you need both eyes on the road! It was featured in the movie Two Lane Blacktop, and Harrison Ford jumped from the dam here in The Fugitive. North of here Maryville, Tennessee is worth visiting as a potential retirement town.

More Great Roads
While searching the Internet for great scenic roads we also saw plenty of references to even more. We’ve listed some here for possible inclusion on your bucket list.
– Trail Ridge Road – Colorado
– North Shore Drive, Minnesota
– Bluebonnet Trail, Texas
– Skyline Drive – Shenandoah National Park
– Natchez Trace – Tennessee and Mississippi

Section of the Natchez Trace in Mississippi

Section of the Natchez Trace in Mississippi

– Columbia River Gorge (Washington/Oregon)
– Hawaii Belt – The Big Island
– Finger Lakes region of New York
– Seward Highway (Seward to Anchorage, Alaska)
– The San Juan Skyway – Colorado.
– The Brandywine Valley trek – Pennsylvania and Delaware.
– Cumberland National Highway (US 40) – Maryland and Pennsylvania

Bottom Line
One of the best things about retirement is your chance to work on checking off your bucket list items. If driving some of the most scenic roads in America is on your list, start working on these, plus any we might have overlooked! And while you are out, check out some of the neighboring retirement towns (you will find plenty of them in our State Directories).

Please share your ideas and comments about your favorite scenic highways, both in the U.S. and around the world, in the Comments section below.

For further reference:
Top 5 Scenic Highways in the U.S.
Your Bucket Lists Are Amazing

Posted by Admin on July 14th, 2014


  1. I’ve done several of these scenic drives and they’re great. There are also some wonderful ones in Canada.

    I highly recommend National Geographic’s Guide to Scenic Highways & Byways for more ideas.

    by Linda — July 15, 2014

  2. These sound like a ” must do” for our early retirement years when road travel is still a good idea! Having watched my parents’ driving skills decline in their late 70’s, I am wondering what the average age is for turning in the drivers’ license? When should long road trips be ruled out as a good idea? As an aside, the three trips in New England – Mass., NH, and Maine- should never be considered during the summer – traffic will have you sitting and going nowhere.with the mass of tourists that descend us in July and August. Of course biking those routes is an alternative!

    by SandyZ — July 16, 2014

  3. Let me add the Taconic Parkway in New York to this excellent list. I ride my motorcycle there every chance I get. It’s as beautiful as the Natchez Trace, and it’s amazing to have a gorgeous, non-travelled road so close to New York City.

    by Michael — July 16, 2014

  4. Great scenic drives for family, friends and creative inspiration.

    by SAGE — July 16, 2014

  5. We loved the drive to Islamorada!

    by SAGE — July 16, 2014

  6. I think you may have left out the greatest road trip of them all — Route 66. From Chicago to LA, you can see virtually all the varieties of geography mentioned in each of the trips above, and have the fun of reliving a bygone era of truly American history.

    Editor’s note: Jim – great suggestion. And best of all, do it in a classic Corvette – just like in the TV show!

    by Jim — July 16, 2014

  7. Route 6 on Cape Cod is the main road that runs from the Canal to PTown … but it misses the true flavor of the Cape that you can only get on Route 6a which runs from the Canal to the Orleans Rotary. It’s called various names along the way but for about 30 plus miles you’ll be up close and personal with antique homes, stone walls, old churches, tiny little village centers, charming inns and B&Bs, small art galleries and shops and any number of quiet little side roads and country lanes that lead to the occasional harbor or view of Cape Cod Bay that are invisible from Route 6. Beyond the Orleans Rotary Route 6 is pretty much your only choice to PTown as it passes through less settled country and eventually passing wild dunes and beach colonies while providing glimpses of the ocean on one side and the bay on the other. Go. Definitely go.

    by rob earl — July 16, 2014

  8. One more great road trip is the Brockway Mountain Drive which winds along the spine of the Keweenaw Peninsula of Michigan’s Upper Peninsula. Built during the Great Depression, it has awesome views. More here : .

    by CJB — July 16, 2014

  9. I don’t think you can beat the Blue Ridge Parkway. I have driven almost all 469 miles of it plus all of the Skyline Drive at the north end of the Parkway. Beautiful and so many things to see and do along the road. Never boring.

    by Phyllis — July 16, 2014

  10. In May this year we drove from Minneapolis to San Francisco via the Badlands, Mt. Rushmore, Devils Tower, the Bighorn Mountains (spectacular views but be sure to watch the road!), Cody, Yellowstone, Reno/Carson City and Lake Tahoe. Really great road trip!

    by MARY — July 16, 2014

  11. How could you possible write an article about great road trips and not mention the Blue Ridge Parkway?

    by Todd — July 16, 2014

  12. I would add the Needles Highway in the Black Hills. Very interesting rock formations. Not a long drive but mixed with the wildlife it is very scenic.

    by Craig — July 16, 2014

  13. This June I took a month off from work and did the Blue Ridge, Skyline Drive, Seaway along Lake Ontario, the coast from Salem Mass to Kittery, Maine, the Loop in Acadia, and the Bay of Fundy in Campobello, NB. All total 5200 miles. What a great time and wonderful views of 2 diverse and awesome countries.

    by Janet Mitchell — July 16, 2014

  14. Another great drive is along Interstate 84 from Portland, OR east through the Columbia River Gorge. The first 45 miles are very lush and verdant with multiple waterfalls until you hit the high desert between Hood River and The Dalles. Following the Columbia River is an absolute treat with the beauty it has to offer.

    by John — July 16, 2014

  15. Has anyone done the Yellowstone/Grand Teton trip? If so, any suggestions

    by linda hyers — July 16, 2014

  16. I just did the tail of the dragon yesterday , twice. You are right don’t take your eyes off the road or your in trouble, real quick. Great road, just don’t do it until you are very comfortable with your bike.

    by Jeff m — July 16, 2014

  17. I agree with John that the Columbia River Gorge highway in Oregon just east of Portland is among the best scenery in the country. Take the old highway, US 30 from Troutdale to beyond Multnomah Falls. Then travel I-84 to Hood River where you take OR State Highway 35 up to Mt. Hood. Travel back toward Portland on US 26 . With one vista after another, you won’t be disappointed.

    by Steve — July 16, 2014

  18. As many time I’ve driven it and as many beautiful roads I’ve been on, the loveliest drive is through Oak Creek Canyon from Sedona to Flagstaff, Arizona.

    by Donna Harrington — July 16, 2014

  19. One of the best vacations was traveling the Natchez Trace. People in Natchez were great.

    by Ned — July 17, 2014

  20. Wow, so many wonderful suggestions. Thank you everyone. They don’t
    call it America the beautiful for nothing. No matter where you go,
    something wonderful awaits.

    by Godsgirl — July 17, 2014

  21. We flew to Fort Lauderdale (easier in and out of then Miami). Rented a car and drove the Keys to Key West.. Stopped half way for lunch in Islamorada then on to mile 0 Key West ! Fun and beautiful 2 week vaca! :cool::cool:

    by Sunlovingal — July 17, 2014

  22. Another totally breathtaking road trip is US 60 between Globe and Showlo Az. About 87 miles you go through a mini Grand Canyon and see other gorgeous scenery as well. It is a truly memorable drive.

    by vicki — July 17, 2014

  23. We drove from West Texas to Paugasset Springs in Colarado. We drove all the back roads to Denver. No highways. Talk about beautiful views of mountains, wildlife, cabins by picturesque streams words cannot tell you how beautiful. Great views around every curve. Try it for yourself, you won’t be disappointed.

    by Florida Bound — July 18, 2014

  24. Top Retirements: I’m looking for a print icon, for a printable version of this article and the comments. Am I missing it? I’ve been to many of these drives and would like to do some of the others as well.

    by Nova — July 21, 2014

  25. New Jersey has a ton of scenic drives. My boyfriend and i are fans of Sunday Drives and used this guide to find the most beautiful routes and stops along the way!

    by Samantha Wanner — March 30, 2015

  26. […] Visit for more great roads. […]

    by 12 best American road trips - The Money Street — April 22, 2015

  27. I’m surprised this article hasn’t had more comments. I know that, having now read it, we will find and ride the Tail of the Dragon — by car. Hwy 12 in Utah is listed (for good reason) but reference to lunch at Hell’s Backbone Grill should be extended. Another fantastic ride is Hell’s Backbone. Not a lot of views until you get to the top, but the one lane bridge is a thrill in itself! Fortunately, the dirt/gravel road continues to be maintained and the bridge was rebuilt in recent years.

    Also not mentioned is the back side of Oahu! When we drove this about 20 years ago, rental cars were forbidden — but we made it! Drive slow and carefully — it is a fitting conclusion to the Road to Hana.

    by Rich — August 10, 2016

  28. Rich, actually I recommend spending the night there. Then you get dinner and breakfast at Hell’s Backbone Grill! They’ll also pack you a lunch for the road. Great place!

    by Linda — August 11, 2016

  29. Rich, while you are wearing out your tires(and your elbows) from the Dragon, try to save some time for the Cherohola Skyway. A road I feel, as an avowed motorcyclist, to be much more scenic, and fun. Two wheels or 4. Just don’t go up thataway in the fog. And…if motoring on the Dragon, watch for logging trucks. With all the tight turns(you just might see your own taillights!), The trucks WILL be sharing your side of the road!

    by Doc Stickel — August 11, 2016

  30. I wrote this several years ago:

    A 10-day driving trip in the Pacific Northwest. Terrific road trip!

    by Jan Cullinane — August 12, 2016

  31. On the east coast of the US and Canada it is hard to beat Blue Ridge, Skyline, Diamondback, Cherohala, TOTD and the Cabot Trail on Cape Breton. If you do drive the Cabot Tr the best direction to use is when the sun is at your back. As others have said, be very careful on the TOTD, depending on the day there can be lots of bike/car clubs and radar that vigorously enforces the speed limit and for good reason. There have been lots of accidents due to one bike/car just slightly crossing the yellow line.
    Lots of phenominal drives through NM, Utah and the coast but I still like hwy 1 btn San Fran and Morro Bay.
    This fall or next spring we’ll take the ’72 Corvette convert. down Rt 66 (what’s left of it). Will pick it up somewhere btn Chi and St Louis then at Flagstaff head north up throgh some of the great drives in Utah and Dakotas.

    by Greg Hurst — August 12, 2016

  32. Thanks, Doc. We have traveled extensively by car in all of that area (and I have hiked much of it also including the AT through the Smokies), but as you know, it becomes a huge place when you are on the ground there. And we never got to the Cherhola Skyway — will do! For anyone who has not been in that southern NC/TN border area (or you only flew in/flew out, or just visited Asheville, etc by interstate) a week or longer “off-highway” trip in that area will open your eyes to the wild and beautiful country Doc and I love.

    And Jan, you trip looks like a gem — I hope others will follow you. My wife and I traveled by car to almost all the areas you went (excepting Mt. St. Helen’s) as well as much more on our 2010 western double-loop trip which covered 10,700 miles over 6 weeks. The Northwest is an incredibly beautiful and varied part of the country. Browsing through your trip made me want to go back and start again. For those who do manage to get to that part of the country, a trip around and into Olympic National Park with a side trip out to Cape Flattery (the western-most tip of the continental US) is both stunning and amazing! That circuit will take several days to a week in itself, but you will find nowhere else in the country to compare to it. If you live in WA or OR and have not taken advantage, shame on you! :<)

    by Rich — August 12, 2016

  33. Thanks, Rich. Olympic National Park and Cape Flattery sound like a perfect combination. And, if you’re 62 or older, purchase a lifetime $10.00 Senior Pass “that provides access to more than 2,000 recreation sites managed by five Federal agencies, with up to 100% of the proceeds being used to improve and enhance visitor recreation services.” Best deal out there.

    A link about the pass:

    by Jan Cullinane — August 13, 2016

  34. We have a 43′ Class A motorhome and a question to each of you who have driven any of these roads. Would you suggest we NOT take the motorhome on any of these? I already know we should avoid the Tail of the Dragon.


    by Norman Roush — August 14, 2016

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