🍁 Falling into Traditions That Last: Northern Virginia and DMV Fall Happenings

There’s something magical about autumn in the DMV — crisp air, golden leaves, pumpkin spice everywhere, and the chance to slow down a bit with family and friends. Megan here, fresh off planning some fall activities, and Shelby can’t wait to get outside with her camera again. It’s tough to be a photographer who can’t use a shoulder — but no worries, physical therapy is going well, and she’ll be back at it soon. Whether you’re new to the area or you’ve lived here forever, fall gives us an excuse to explore, connect, and build memories. And of course our favorite part, is capturing all of the joy and sharing it with you!

Below we’ve pulled together a curated list of some of the best fall events in Prince William, Loudoun, Fairfax, and beyond — family-friendly, festive, and full of tradition.

🍂 Nothing says fall like diving into a giant pile of leaves! 🍁
📸: Shelby Leigh Photography, LLC

These are some of our favorites for this season (late September through mid-November). We’ve grouped them so you can pick what fits your vibe or schedule. And trust us, this is a short list! Wherever you are in the DMV, take some time to scout out what activities work best for you and your family!

🌾 Outdoor & Farm-Style Fun

• Great Country Farms Fall Pumpkin Harvest (Loudoun area)
  A staple for folks who love pumpkin patches, cider donuts, hayrides, and picking pumpkins. (Dates: full October, likely through end of the month; check local site for exact calendar.)

• Leesburg Animal Park — Pumpkin Village Fall Fest (Loudoun County)
  Opens September 20, 2025, through November 4. Preview weekend September 13-14. Attractions include giant hill slides, moon bounces, wagon rides, a corn bin, pedal carts, lots of animal encounters (petting, feeding), pony rides, weekend entertainment, seasonal food, and more.

• Cox Farms Fall Festival (Centreville / Fairfax County)
  Runs September 20 – November 9, 2025, open 10 a.m. to 6 p.m. in September & October, and 10 a.m. to 5 p.m. in November. Closed Tuesdays & Wednesdays. Their Fall Festival includes hayrides, the “Cornundrum” cornfield maze, giant slides, goat village, huge pumpkins, rope swings, toddlers’ play zones, live music, and much more. Big hit for families.

🎉 Festivals & Community Events

• Reston Multicultural Festival (Reston, Fairfax County) — celebrate the many cultures that make up our community with food, performances, kids’ activities. (September 20)

• Bluemont Fair — art, crafts, jams, music in Bluemont; lovely chance to wander, shop local, eat good food. (September 20-21)

• Leesburg Air Show — aerial performances, static tarmac displays, kids activities, food and fun. (September 27)

• Vienna Oktoberfest (Vienna, Fairfax County) — music, food, and festive atmosphere. (October 4)

• City of Fairfax Fall Festival — crafts, kids’ play, everything to make an easy afternoon of fall fun. (October 11)

• Manassas Fall Jubilee (Prince William County) — heritage crafts, food, music, community feel. (October 5)

• Haymarket Day 2025 — a lovely hometown city-wide street festival, complete with parade, performances, live music, delicious food and fun. (October 18)
  (we’d totally be remiss not to mention this one, as we love the small “Stars Hollow” vibe of our town!)

🍷 Arts, Wine, & Evening Events

• Fall Wine Festival & Sunset Tour at Mount Vernon — beautiful backdrop, good for couples who enjoy a relaxed evening with views and wine. This one may sell out, so get your tickets early if you plan to go. (October 10-12)

• Mount Vernon Fall Harvest Festival — bring the kids! Seasonal foods, crafts, tours of gardens, beautiful foliage to enjoy. (October 18-19)

• Waterford Fair — arts and crafts fair, picturesque setting (historic village). (October 3-5)

🎨 Arts & Crafts / Markets

• Heritage Harvest Festival at Loudoun Heritage Museum — offers a blend of history, harvest, and artisanal crafts. (September 27)

• Fall Festival + Artisan Market at Fairfax Corner — shop local artisans, seasonal food, family-friendly environment. (October 18)

• Occoquan Fall Arts & Crafts Show — browsing vendors, nice walk, food options, good for a laid-back weekend. (September 27-28)

👍 Why Fall Events Make Great Tradition

Shelby here: there’s more to fall than pumpkins and leaves. These events are how traditions begin — the moments when kids’ faces light up on the hayride, the smell of cider donuts, that chill in the air just before sunset. They’re simple, but rich. Visiting the same farm, walking through the same fair every year, learning new things about your county — it builds roots.

Megan adds: for us photographers, fall is also one of the most magical seasons for lighting, color, and capturing warmth. Getting out to these events is a way to slow time, to see familiar places in new light. And for your family or friend group, these can become “the thing we do every fall.” Something to to look forward to.

🔎 Know…Before You Go

• Always check event websites or social media beforehand — times, ticketing, or even schedule shifts can change. And as much as we hate to admit it, once in a while, we may get it wrong, too! We try hard to get it right, but better safe than sorry as we don’t want to be responsible for a date mistake!

• Dress in layers. Fall mornings are crisp, afternoons warm, and evenings chilly.

• Bring cash or small bills if there are artisan vendors or food trucks — sometimes payment options are limited.

• Weekdays or preview weekends can be less busy, more relaxing if you want a calmer experience.

🌟 Which Event Should You Pick First?

If you’ve only got one weekend, here are two we think are must-does:

1. Great Country Farms Fall Pumpkin Harvest (Loudoun area)
   A staple for folks who love pumpkin patches, cider donuts, hayrides, and picking pumpkins. (Dates: full October, likely through end of the month; check local site for exact calendar.)

2. Pumpkin Village at Leesburg Animal Park — great mix of animals + classic fall fun + photo-friendly settings.

3. Bealeton Hot Air Balloon Festival — mostly because we wanted to make sure you are paying attention to ALLLL of the activities offered…and, it’s on our bucket list!

Let us know what you end up doing! If you go, share your photos. If you have an event we didn’t list but love, we’d love to hear about it.

Affordable Adventures: Travel Tips That Won’t Break the Bank

Let’s bust a myth right away: You don’t have to be rich (or retired) to travel well. With a little intention and some strategic planning, you can enjoy incredible adventures without draining your savings account. From cash back tools to credit card perks to point strategies, here’s how we make travel work for our budget — and how you can too. We’re breaking down the practical and the lesser-known ways to save, plus real-life examples from our own trips.

1. Points Are Your Passport: Make Your Spending Work for You

One of the easiest ways to make travel more affordable is to earn points or miles on the money you already spend. Two of our favorite cards for this are the Capital One Venture Rewards Credit Card and the American Express Platinum.

• Capital One Venture offers 2x miles on every purchase. The real win? You can erase travel purchases using points, or transfer them to airline and hotel partners.

• Amex Platinum is ideal if you fly often and value perks like Centurion Lounge access, airline credits, hotel upgrades, and 5x points on flights booked through Amex Travel.

Real-Life Example: We booked round-trip flights to San Juan, Puerto Rico using American Express points, covering over $500 in airfare with points alone. I can’t remember exact flights at the moment, but I know we’ve used points for free airfare before we even started Shutter and Compass. So, If you aren’t using those credit cards in this way…here’s your sign to start. NOW!

Tip: Keep an eye on sign-up bonuses. These often range from 60,000–100,000 points when you meet minimum spending requirements — enough to cover one or two round-trip tickets!

2. Rakuten = Free Money for Travel

We try to use Rakuten every time we shop online. We’re getting better, but you can see that we have a long way to go to fully maximize it — but, we still believe every little bit helps! Rakuten is a cash back platform that gives you money back just for clicking through their site to see if where your shopping is a partner, before you buy from stores like Sephora, Walmart, or even travel sites like Expedia and Booking.com.

If you haven’t tried it yet, here’s our referral link to get started and score a welcome bonus:
👉 Rakuten Referral Link

Insider Tip: Link your Amex or Visa card to earn in-store cashback at places like Ulta and Walgreens, and if we just realized it works for Giant, too! So…all those groceries…Dominion Valley and Haymarket people, I’m talking to you…go ahead and link it for those points!

RAKUTEN POINTS

It’s not a ton, but honestly, we’re still excited we’re getting paid for literally our regular shopping trips.

If you haven’t tried it yet, here’s our referral link to get started and score a welcome bonus:
👉 Rakuten Referral Link

How we use it: When we started our Rakuten account in November, 2024, we earned 4,000 points just to start, and then we quickly added points, without even realizing it! From our regular purchases (some even in-store!) at Adidas, Giant (again - how cool!), Shutterfly, Madison Reed (because…hello, we’re in our 40’s) and legit, I JUST saw that my TACO BUENO purchases in Oklahoma earned me points…all because my American Express is linked. Like really, why would one NOT do this?! while you can convert the points to dollars, we actually send them right over to American Express to keep as points for our travel. I know that there’s a mathematical or better way to figure out what works best, but this is what we’re choosing for now. While I know I still need to thank her, I know I’ve read a lot of my travel credit card information from Jen Woodhouse - https://jenwoodhouse.com/category/travel/ - I’ve known Jen for somewhere around a decade, and she’s the real deal. Excited to hopefully connect soon (once she’s in the country for a hot minute from all of her travels) so we can learn more from her! But we highly recommend checking her site out — she is incredibly knowledgeable. Like really — not just in travel. She does it ALL!

3. Stack the Savings: Cashback + Points + Coupons

Combine these methods for serious savings:

• Use Rakuten (or a similar browser extension like Honey or Capital One Shopping).

• Book with a rewards credit card.

• Search for discount codes or use hotel loyalty programs (e.g., Hilton Honors).

Pro Tip: Book your hotel through Rakuten, use your Amex to pay, and make sure it’s a property you can earn hotel points on. That’s a triple win.

4. Fly Smart: Timing is Everything

• Fly midweek. Tuesdays and Wednesdays often have the best fares.

• Set fare alerts with tools like Google Flights or Hopper.

• Travel off-season or during shoulder seasons (e.g., late April or early October).

You can score $49 one-way fares on Southwest just by flying on a Wednesday in October — peak weather, low prices.

5. JGOOT: Just Get Out of Town

We’re just diving into JGOOT (Just Get Out of Town) — a subscription-based platform that teaches you how to use points and find mistake fares. So far, we’re impressed by how it encourages thinking differently about travel. Definitely legit, and depending on your needs, they can walk you through an amazing process for making your travel not only more affordable, and also getting you into those business class and luxury flights!

JGOOT teaches:

• How to book flights with fewer points by transferring to partners.

• How to find deals where points are valued 2-4x more than booking directly.

We haven’t booked a full trip using it yet, but we’ll report back when we do! It’s worth checking out if you want to level-up your points game.
https://www.jgoot.com

6. Look Local First

Adventure doesn’t always require a passport.

• Check your state’s tourism board for discounts and deals.

• Plan a short road trip to a nearby vineyard, historic town, or hiking trail.

• Search Airbnb Experiences or Groupon for things to do within 2 hours of home.

Some of our favorite days have been 45 minutes from our doorstep. If you’re in Northern Virginia, this is your healthy reminder that you are likely within an hour or two from our Nation’s Capital, Washington DC. There is always so much to see and do there. And what we’ve noticed is that a lot of people who have lived here the longest, STILL haven’t been to our Nation’s Capital. Y’all are missing out! BUT, no fear. If the DC traffic and city life are either intimidating or just aren’t your thing, there are so many beautiful wineries, breweries, restaurants, hiking trails, and so much more close by.

7. Use Travel Communities for Deals and Ideas

Facebook groups, Reddit threads (like r/travelhacks), and even TikTok are full of travelers sharing real-time deals, itineraries, and budget tips. Join the conversation, ask questions, and share what’s worked for you. And as always, hop on over to https://www.facebook.com/groups/shutterandcompass to share your thoughts and questions, or even share about your latest travels and awesome finds.

8. Create a "Travel Fund" Jar (Seriously)

Yes, we love points. But nothing beats cash.

• Start with $10/week.

• Add every time you skip a takeout meal or cancel a subscription you’re not using. Also, if you haven’t canceled those subscriptions you aren’t using…go do that!! You may be shocked by how much you’re not even realizing you’re spending. >>>ask us how we know<<<

We’ve funded everything from cruise excursions to a new carry-on just with what we stock l away over a few months.

You Can Afford to Go

Whether it's a luxe cruise booked with miles, or a weekend Airbnb funded by cashback and a travel jar, there are so many ways to make adventure more accessible.Start where you are. Use what you have. Learn a few new tricks along the way. And remember, a good hike, a free museum…those are still in our travel realm! Enjoy what you can, when you can. And remember: it doesn’t have to be extravagant to be meaningful. Just go and make the memories. You’ll thank yourself (and us!) when you realize how much you love it.

XO,

P.S. We’re working on a future post specifically about how to maximize credit card points like a pro — so stay tuned! Let us know what questions you have so we can get some guest speakers lined up and so we can share more with you!

Disclosures: We may earn a small commission when you use our affiliate links, including Amazon and Rakuten. This comes at no cost to you and helps support future content for Shutter and Compass. Thank you for your support!