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
A hotel that’s also a free 24-hour contemporary art museum penguins included. We booked a Corner Suite at 21c and it was massive: separate bedroom, living room, dining area, 699 square feet to spread out in. The bathroom alone had a double vanity and custom Rookwood Pottery tile that made getting ready weirdly entertaining.
The location is downtown, two minutes from Fountain Square, walkable to Boca for dinner, and close enough to hop the free streetcar into Over-the-Rhine. If OTR is where most of your plans are, you might want to stay closer to that neighborhood instead downtown worked for us, but we spent more time in OTR than we expected to.
And yes, there’s a recycled-plastic penguin sculpture that will absolutely scare you the first time you open your door and forget it’s there. Link in bio for the full review rooms, parking, walkability, and everything else before you book 🎨
Three neighborhoods, one streetcar, and more Cincinnati specialties than I could finish in one afternoon.
We hit a goetta breakfast sandwich, chocolate chip ice cream from a shop that’s been at it since 1870, a Liège waffle that earned its Diners, Drive-Ins and Dives spot, and Cincinnati chili the way it’s actually meant to be eaten... over a hot dog, buried in shredded cheddar.
$75 got us three and a half hours, a local guide, free streetcar rides, and a genuinely full stomach. Don’t eat breakfast before this one, the portions add up fast.
My third Secret Food Tour in my third city, and it’s still undefeated.
Link in bio for the full review cost, route, parking, and every stop we hit 🥟🌶️
13 creek crossings, a canyon that keeps closing in around you, and a hike I’d genuinely put back on my itinerary, West Fork Trail was the one.
We got to Call of the Canyon at 7:15am and the lot was barely a quarter full. By 12:30 it was 85% full, so if there’s one tip that matters most, it’s this: go early.
The maintained trail is 6.6 miles round trip, mostly flat, mostly shaded, but I kept my regular tennis shoes dry the whole way by hopping across the rocks at each crossing. It’s rated moderate, and honestly that’s about the distance, not the terrain.
Here’s what nobody tells you though ✨ the maintained trail isn’t the end. We changed into water shoes at the official endpoint and kept going another mile straight through the creek, canyon walls narrowing around us the whole time. That extra mile ended up being my favorite part of the entire hike.
5/5 for me. I’d bring the water shoes again in a heartbeat.
Link in bio for the full guide parking, timing, what to pack, and everything I wish I knew before I went 🥾
Two hours, zero regrets. The Pink Jeep Broken Arrow Tour is hands down one of the most fun things we did in Sedona.
Open-air Jeeps crawling over slickrock, backcountry views you can’t reach on your own, and the famous Road of No Return, steep, thrilling, and somehow completely safe the whole way down.
If you’re picking one paid activity in Sedona, make it this one.
You have to do @pinkjeeptours 🌵🚙 Link in bio for the full review.
Dinner beside Oak Creek at Cress, and yes, it’s a splurge, but I’d do it again in a heartbeat.🤍
Candlelit tables under the trees, the creek running right beside us, a menu that mixes Arizona ingredients with French technique. We ordered a little of everything: the squash and beet salad, milk rolls with three different butters, sweet potato gnocchi that somehow felt light instead of heavy. Then two desserts because we couldn’t decide. The Vanilla Crème Caramel with Manchego cheese completely stole the show, salty and sweet in a way that sounds strange until you taste it.
Plan on $100–250 for two depending on what you order, and this isn’t the spot for a quick casual dinner, it’s slow, intentional, and worth every minute. Book ahead and ask for a creekside table if you can.
If you’re looking for one unforgettable meal in Sedona, this is it. Link in bio for the full review 🍽️
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