Pete Tolsdorf, creator of SkiTripPlanner.com. Photo provided by Pete Tolsdorf.

Scott: Hi Pete, thanks for participating in the DCSki Interview Series. You recently launched the ski resort ranking site SkiTripPlanner.com. How is your site different from other ski resort rankings?

Pete: The ski resort rankings at SkiTripPlanner.com are personalized to you — what you like and what you want from a ski resort. You select the criteria that match your interests and preferences, and the site generates a list of ski resorts that best fit your selections. This is the choose-your-own-adventure approach to ski resort rankings.

Do you prefer beginner terrain and enjoy top-notch customer service and plentiful nearby restaurant options? Then your top results would be Steamboat, Deer Valley, and Beaver Creek. Or are you an expert skier seeking deep powder, expert terrain, and great tree skiing? Then the site would recommend Jackson Hole, Whistler-Blackcomb, and Palisades Tahoe. The results also include a match score that shows how closely the resort aligns with your selections.

Other rankings of “Best Ski Resorts” use static criteria and fixed category weightings. Unless your criteria closely align with the established ranking criteria, the list won’t be right for you. Some other publications use reader surveys, which reflect the resorts that their readers like, but maybe not what you like.

Scott: I’m curious to learn more about your background and what led you to create the site. When did you first start skiing?

Pete: My early days of skiing were at local hills near my childhood home in Connecticut. I have fond memories of learning to ski at Oh-Ho-Ho, a Christmas-themed learning hill in Woodstock, Connecticut. I remember the rope tow was an actual fiber rope powered by a diesel truck engine in a woodshed. It has since closed, sadly, like so many other smaller ski areas throughout New England.

My early love of skiing led my parents to start taking my sister and me to Vermont on winter weekends. I joined the junior race team at Okemo in elementary school and raced throughout Vermont until high school. I then raced for my high school team.

Scott: What was it like skiing in Vermont back then, and how has that changed over the years?

Pete: Most ski areas in Vermont in the 1980s and 90s were independently owned and operated, including Okemo. The owners, Tim and Diane Mueller, were regulars on the mountain. You would see them on the slopes or in the lift lines and could say hi and have a conversation. Their love for and commitment to Okemo showed in everything they did.

In recent years I have skied at Okemo and the many other Vermont ski areas from my junior racing circuit. Industry consolidation through the multi-mountain passes has changed the ski resort landscape, for good and bad. The flexibility of being able to ski dozens of different resorts on the same pass is great. But some of the local flavor and customer service has deteriorated, and lift lines on peak days have grown.

Scott: I understand you have passed your love of skiing to your two sons. Did they immediately take to the sport?

Pete: They did, and it has been so rewarding. I taught both sons to ski at Whitetail. I was eager to start them at a young age, but the minimum age for kids’ lessons at Whitetail was seven. I didn’t want to wait that long. So, starting when each of my sons was three, we would wake up early on Saturday mornings, drive from Arlington to Whitetail, and do laps on the magic carpet.

When they fell, I would just pick them up and they would try again. They were learning so many other physical skills by trial-and-error at that age, so I figured they could do the same with skiing. By the time they were old enough for ski lessons, we were skiing the whole mountain together.

Pete’s two sons have been skiing since they were three. Photo provided by Pete Tolsdorf.

Scott: You told me that you’ve skied at nearly 100 resorts across the country. But the Mid-Atlantic is in your backyard. What are some of your favorite resorts closest to D.C., and how often do you visit them?

Pete: After the early days at Whitetail from 2016-2020 and some trips to Liberty, Roundtop, Snowshoe, Wisp, and Massanutten, we tried Timberline in West Virginia in 2021 and fell in love with it. We have skied there most winter weekends ever since. Timberline receives an average of over 100 inches of natural snow each winter, has great snowmaking, a fast base-to-summit high-speed six-person lift, and is less crowded than the other regional resorts.

Scott: How many trips outside this region do you make each season?

Pete: Usually two or three, and I usually ski several different resorts on each trip.

Scott: Having visited so many areas in New England and out West, I’m guessing you developed your own internal criteria for picking which resorts to visit, and that undoubtedly planted the idea for creating SkiTripPlanner.com. Is that right?

Pete: Although I have my favorite ski areas, I love the novelty of skiing somewhere new for the first time and learning the terrain, the town, and the spirit of the place. The idea for SkiTripPlanner.com came last year during a ski trip with friends to Utah. The group had skiers and riders of different abilities and interests. I had skied at each of the resorts we were considering, so I shared my perspectives on the pros and cons of each. But not everybody agreed on what was a pro and con. So we did our best to select the resorts that best aligned with the group’s preferences.

This process made me realize how helpful it would be if there were an online resource that could allow users to enter in their preferred criteria to generate custom recommendations to match their preferences—for themselves, their families, or their friend group. I searched for existing sites but found nothing like what I was envisioning. So, I decided to build it.

Pete has skied at nearly 100 ski areas across North America. Photo provided by Pete Tolsdorf.

Scott: One thing I really like about SkiTripPlanner.com is its simple, uncluttered design. It presents skiers and snowboarders with simple filters they can utilize to dial in their preferences in areas such as terrain, weather, scenery, food and drink, and participation in multi-resort passes. What has been your design philosophy for SkiTripPlanner.com, and how did that philosophy translate into the site we see today?

Pete: That’s great to hear! My design philosophy is simple: to create a smooth and user-friendly journey from criteria selection to search results. I think we are all tired of websites that assault our senses with flashing ads and click bait. SkiTripPlanner.com is ad-free, you don’t need to set up an account to use it, and it’s free to use. That was all intentional. Revenue generation comes solely from hotel commissions that I receive from the integrated lodging booking map on each resort page.

Scott: Underlying the site is a database you’ve built to enable users to perform these customized searches. How did you gather the criteria to input into this database, and how long did that take?

Pete: I sought to cover the full range of criteria that skiers are riders might consider when deciding where to take a ski trip. I then grouped the 44 options into six major categories. On the site, users can quickly tab back and forth among the various major categories and individual criteria. It took a few months to refine the criteria to a point where I felt it was comprehensive but not overwhelming.

Scott: How often do you need to make updates to the underlying data?

Pete: A fun part of maintaining the site is keeping up to date on ski industry news and resort developments, including at great sites like DCSki.com! I typically make several updates per month to keep the information current.

Scott: Many of the metrics you use are objective (such as average annual snowfall and terrain composition), while others might be at least slightly subjective (such as scenery or level of customer service). Are these criteria primarily rooted in your own personal experience? What other types of information do you gather to categorize resorts?

Pete: I based the ratings for the subjective categories on three sources: editorial perspectives from a broad range of reputable ski industry publications; an algorithmic synthesis of tens of thousands of user reviews across several online platforms; and my direct personal experience at the resorts. I was surprised and encouraged to find significant alignment among these sources, especially among the top 25 results in any given category.

This process also led me to create the “Top Resorts” section of the website. That page has my take on the Top 10 resorts in a range of subjective categories. I applied my dad humor skills as best I could to the category titles.

Scott: Right now, you have 114 resorts represented on the site, with a focus on larger destination resorts to the west and north. Do you think you might expand someday to include resorts beyond North America?

Pete: Someday, I hope! Skiing in Europe and Japan is a whole different world. I am not there yet, but perhaps that could be a great future expansion of the site.

Earning some turns. Photo provided by Pete Tolsdorf.

Scott: What has been some of the feedback you’ve received since launching SkiTripPlanner.com?

Pete: The personal feedback from skiers and riders has been uniformly positive. The responses from online sources like Facebook and Reddit has also been really encouraging, especially considering those sources are not usually wellsprings of positivity. Users have remarked on how closely their top search results match their actual preferences.

Scott: Do you have any plans you can share about future enhancements you’d like to make to the site?

Pete: I would like to add trail map links and include additional photos of each resort on the resort pages. If your readers have other ideas, I welcome them either in the comments section or at support@skitripplanner.com.

Scott: This looks like a passion project for you. What has been the most rewarding aspect of creating SkiTripPlanner.com?

Pete: The creative process of building the site was more fun than I expected. I was fortunate to have worked with an exceptional creative and website development team at Dialogue Theory (www.dialoguetheory.com). I highly recommend them for any website needs your readers may have.

But the most rewarding part has been helping to promote a sport I love and to support that experience with people I’ve never met and probably never will.

Scott: What is your professional background, and outside of skiing, what are some of your other hobbies and passions?

Pete: I am a lawyer with an environmental nonprofit based in Washington, D.C. In addition to skiing, my hobbies include biking (road and mountain), coaching youth soccer, and helping with my sons’ sports and extracurriculars.

Scott: What tips would you offer a Mid-Atlantic skier who is thinking of making their first ski trip outside this region?

Pete: Consider resorts beyond those with widespread brand name recognition. Now more than ever, those resorts are very overcrowded and expensive. In your search on SkiTripPlanner.com, consider selecting the options for “Less Crowded” and “Off the Beaten Path” together with your other criteria. Resorts that are farther from major metro areas and major airports can also offer great terrain with much shorter lift lines, more elbow room, and a more relaxed experience.

Also, don’t overlook resorts in the Canadian Rockies. The skiing is amazing, crowds are low, and everything is much less expensive than in the Western U.S. Same for Europe. Departing from the D.C. area, flights to Europe are not that much longer than to the Western U.S., the skiing is great, and the food is fantastic. Lift tickets are affordable (about 1/3 the cost of major U.S. resorts), and some of the resorts are even on Epic and Ikon.

If you’re going out west or to Europe, mid-March through mid-April is a great window. Lift lines are much shorter (especially in early April), most resorts are still fully open with great base depths, the days are longer, it’s sunnier, and the vibes are good.

And avoid skiing during Christmas week, MLK weekend, and Presidents’ Day weekend if you can. If you have school age kids and that’s the only time you can go, then still go, but if you have flexibility to go at any other times, it’s a better experience in nearly every way.

Pete and his family on a ski trip. Photo provided by Pete Tolsdorf.

Scott: And finally, I’d like to ask you to reflect on your many days of skiing. What was one of the best ski trips you have taken, and what made it so special?

Pete: My favorite trip was the most recent one over two weeks at the end of 2024 and start of 2025. My family and I covered several resorts in Alberta and British Columbia. The highlight was Revelstoke, which has North America’s largest vertical drop, gets tons of snow, and has great high alpine bowls and exceptional tree skiing. It is uncrowded, scenic, and sits above an authentic mountain town.

Scott: Any other final thoughts you’d like to share?

Pete: Thank you for the opportunity to be featured on DCSki.com! The site is a fantastic resource for Mid-Atlantic skiers and riders. You and your team bring such great news and insights to the skiing community in this region. It has been a privilege to be featured here and to be able to share SkiTripPlanner.com with your readers.

Scott: Thank you Pete.