Boston is one of those cities that just feels alive when there’s an event happening — and there almost always is. Whether it’s tens of thousands of flags fluttering on Boston Common in May or confetti raining down during a North End feast in August, Boston knows how to celebrate.
Here’s my guide to the best Boston festivals and holidays — from patriotic moments that will give you goosebumps to foodie events you’ll be talking about for years.
If you’re in Boston for Memorial Day weekend, make your way to Boston Common. Every year, Home Base volunteers plant 37,000 flags on the Soldiers and Sailors Monument hill — one for each Massachusetts service member who has died in the line of duty since the Revolutionary War.
It’s quiet, powerful, and absolutely breathtaking. If you’re a photographer, go early morning or at golden hour to catch the soft light across the sea of flags.
Patriots’ Day (the third Monday in April) is uniquely Boston — it commemorates the battles of Lexington and Concord and doubles as Marathon Monday. The Boston Marathon is the world’s oldest annual marathon, and even if you’re not running, being part of the cheering crowd is an experience.
Head to Boylston Street near the finish line or plant yourself in Brookline or Newton to catch the runners tackling Heartbreak Hill.
Boston takes Independence Day seriously — and what better place to celebrate than one of the birthplaces of the Revolution?
Head to the Charles River Esplanade for the Boston Pops Fireworks Spectacular. It’s an all-day event with live music, picnics, and one of the best fireworks shows in the country.
Boston’s North End is already basically Italian Disneyland, but during St. Anthony’s Feast, it levels up. The last weekend of August, Hanover Street is closed to traffic and filled with food stalls, confetti parades, marching bands, and crowds of hungry locals and visitors.
This is New England’s largest Italian festival, and it’s been going strong for over 100 years.
What to eat:
Arancini (fried rice balls)
Italian sausages with peppers & onions
Zeppole (Italian fried dough)
And, of course, a stop at Mike’s or Modern Pastry for a cannoli
Pro tip: If you want a quieter North End experience, avoid this weekend — but if you want to be in the heart of the party, this is the time to go.
If you’re visiting during August, don’t miss my guide to If you’re visiting during August, don’t miss my guide to St. Anthony’s Feast in Boston’s North End—it’s one of the city’s biggest annual celebrations.St. Anthony’s Feast in Boston’s North End—it’s one of the city’s biggest annual celebrations.
The third weekend of October brings Head of the Charles, the largest two-day rowing event in the world. Even if you don’t know the first thing about crew, it’s a beautiful excuse to spend the day along the river, sipping cider and cheering as boats glide by with the fall foliage in the background.
Boston does cozy winter vibes really well. In December, Boston Common is lit up with a massive Christmas tree and holiday lights, and Faneuil Hall Marketplace hosts Blink! — a light and sound show. Add in ice skating on Frog Pond and hot chocolate from Tatte, and you’ve got a Hallmark-movie-level evening.
Boston knows how to throw a festival. Whether you’re standing in awe of 37,000 flags on Memorial Day, eating your way through St. Anthony’s Feast, or bundled up watching fireworks over the Charles, these holidays and events let you experience the city at its most alive.
Plan your trip around one of these celebrations, and you’ll leave with a camera roll full of photos, a stomach full of food, and maybe even a little confetti in your suitcase. For an up-to-date list of annual events, check out BostonUSA’s official event calendar. Planning your trip around the seasons? Read my Best Time to Visit Boston guide to see which festivals align with the best weather
10 stops. One very full day. Zero regrets. Amsterdam has one of the best food scenes I’ve experienced anywhere in Europe, but the honest caveat is that some of the viral spots come with lines that will genuinely test your character. I skipped a few. I regret nothing.
Here’s what actually made the cut on my self-guided Amsterdam food tour:
Fresh stroopwafels at Hans Egstorf: made right in front of you, warm caramel, no line. This one won.
Lourens cookie croissant: flaky outside, gooey chocolate inside. Did not share.
Café Winkel 43 apple pie: one of the rare viral places that fully lives up to the hype.
Davie’s Amsterdam for the Lelie sandwich: pastrami, pickles, marbled bread. Deceptively simple. Absolutely excellent.
De Kaaskamer to end the day: 400+ cheeses, grilled cheese with what they call ketchup (it’s not ketchup, and it’s better), and bunker cheese aged in underground military bunkers.
The full route covers 10 stops through Jordaan, the 9 Streets, the canal district, and the flower market area with a Google Map included so you can just follow along.
Full guide with every stop, tips for beating the lines, and what I’d skip vs. do again | link in bio.
#amsterdam #visitamsterdam #netherlands #travel #visitnetherlands #traveleurope
There’s a version of Gatlinburg that’s all fudge shops and tourist crowds, and then there’s the version that actually makes you want to come back.
Here’s everything worth doing downtown, in the order I’d do it: 🏔️
✨ Start at @gatlinburgskypark before the crowds hit
✨ Walk the strip mid-morning when it’s still manageable
✨ @googooclusters stop (see my post from Tuesday: don’t skip it)
✨ Dinner at one of the local spots off the main drag
✨ Wander back out at night when the lights are on and it gets actually pretty
This isn’t your overscheduled Smoky Mountain itinerary. It’s more of a “here’s what I’d actually do if I had one solid day” kind of list.
Full downtown Gatlinburg guide linked in bio. 🔗
If someone told me I’d spend five hours at SkyPark, I would not have believed them. And yet. 😅
Gatlinburg SkyPark sits above the strip and it’s one of those places that looks like a quick stop on paper and turns into most of your afternoon. The SkyBridge alone is worth it — longest pedestrian suspension bridge in North America, and yes, you will look down.
✨ SkyBridge (longest pedestrian suspension bridge in North America)
✨ SkyLift ride up with views of the Smokies
✨ Walking trails with mountain views in every direction
✨ Way less crowded than downtown
Fair warning: if heights genuinely freak you out, the bridge might not be your thing. The rest of the park is still 100% worth it. Full guide with tickets, tips, and what to skip linked in bio. 🔗
I walked into Goo Goo Cluster in downtown Gatlinburg thinking I’d spend five minutes and leave with a small piece of candy. I was wrong on both counts. 😅
You build your own chocolate cluster at a kiosk: caramel, sea salt, pretzels, cocoa pebbles, you name it, and then watch them make it right in front of you. The whole thing takes about 15 minutes and costs $15.
The caveat? This is not a snack. This is a full-size brick of chocolate that I was still eating two days later.
If you’re already walking the Gatlinburg strip, this is an easy yes. Especially if you have absolutely no self-control around caramel. (Asking for a friend.) Full experience breakdown linked in bio. 🔗
Your Knoxville Airport survival guide, from someone who’s flown through TYS 100+ times is now up on my blog🛫
Parking, TSA wait times, where to grab food before your flight, rental cars, all of it, from someone who actually knows this airport. No guessing, no googling at the last minute.
TYS is small, easy to navigate, and honestly one of the less stressful airports I’ve been through. You just need to know a few things going in.
Full guide linked in bio. 🔗
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