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
Italian food felt like the last thing I expected to find in the middle of the Appalachian Mountains... until I sat down at Ilda in Sylva.🍝
They call it Italian-Appalachian, and that’s not just a tagline. Homemade pasta, craft cocktails, local ingredients pulled straight from the mountains around it, this is the kind of meal that makes you forget you’re two hours from the nearest city. It’s cozy, it’s a little upscale, and it is not a walk-in kind of place, call ahead, because tables go fast on weekends.
It’s not cheap, and it’s not trying to be. But if you’re already making the trip out to Sylva, this is the one reservation worth planning your day around.
Full write-up, including what to order, link in bio.
Booked my fall cabin before September even started, and I’m not sorry about it. 🍂
These are the stays that make you actually want the cold to hurry up fireplaces, mountain views, the kind of porch you don’t leave. Not every one of these is going to fit every trip, but if a cozy fall getaway is on your radar, this is the roundup to start with.
One of my favorite travel seasons is almost here, and I have zero chill about it. 🍁✈️
There’s just something about fall trips cooler air, apple orchards, that first flannel of the season, food that actually makes sense with the weather again. I’m already mentally packing for it before September even starts.
If fall is your favorite time to travel too, tell me where you’re headed... I’m taking notes for the list.
Pack your bags... ✈️🧳My hiking and road trip gear shop just got a refresh, and this is everything that actually earns a spot in my bag. The dry bag pulls double duty for beach days and trail days, the Osprey backpack is the one I grab for anything motorcycle or day-hike related, and the GoPro comes with me literally everywhere at this point.
Nothing on this list is filler it’s all stuff I’ve used, packed, and repacked more times than I can count. Full shop linked in my bio if you want to build out your own kit before your next trip.
Filing this one under “go now before it gets cold.” Bonneville Hot Springs is one of those trips where fall access is honestly the sweet spot the campground road is open, the hike in is short, and you skip the snow-and-gate situation we dealt with when we went in March.
September and early fall mean clearer trails, easier parking, and pools that are just as good without the extra mile of hiking to earn them. Fewer than 10 people out there when we visited, a rustic changing booth, zero amenities, and pools that range from “relax” to “actually scalding” until you move some rocks around and mix in river water. Small waterfalls feeding in, mountains in every direction, not polished, and that’s exactly the point.
Full breakdown on parking, what to pack, and timing it right is linked in my bio.
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