Boston Pride 2025

A Week of Color, Cookies, and Carry-On Charm

Thank you to the brands listed in this article for providing their products to help celebrate the BEST Pride celebration ever.

I just got back from one of the most vibrant, soul-filling, rainbow-sparkled weeks I’ve had in years — Pride Week in Boston. Let me tell you, Boston REALLY knows how to throw a celebration that wraps you up in joy, laughter, and community. I’m still glowing, still slightly hoarse from cheering Happy Pride. And yes, I packed for the whole week in just a carry-on. Yes, me, the person who ALWAYS overpacks, actually used a single carry-on for a wardrobe for 7 whole days. I’ll get to that in a minute, because first, let’s talk about how fabulous this trip really was.

The Adventure Begins — One Bag, Big Plans

So, I don’t usually travel light; I have overpacking issues (like bringing 12 outfits for a 3-day weekend so I have options). On this trip, I flew Breeze Airways, and my ticket (my last FREE flight from the year of free flights that I had won from them), and the ticket they booked for me only included a carry-on. So I challenged myself to pack light (as I hyperventilated over what was left behind).

I need my luggage to be functional but chic, and my Rodeo Drive Hardside Carry-On from Ricardo Beverly Hills is basically the Beyoncé of suitcases. It’s sleek, stylish, and organized like a dream. I packed seven full days of outfits, layers (because let’s be honest, Boston weather is moody), and even a pair of backup shoes. All zipped in tight and ready to roll.

Yes, it’s true. A 71-year-old woman can still pack for a week without checking a bag. That carry-on is lightweight, zippy (no pun intended), and fits in every overhead bin. I glided through the Vero Beach Airport like I was on a fashion runway. TSA didn’t know what hit ’em. It also includes just about everything you can think of, including s2 hoe bags, a laundry bag, a makeup bag that snaps on, a place to put your cell phone charger with a sliding cover to plug in your USB to charge your phone, oh and a GREAT lock (just in case I did decide to check it). It is sturdy!!!!

The Vibe in Boston

There’s something extra magical about Boston during Pride. Maybe it’s the colonial brick buildings draped in rainbow flags, or the mix of old soul and fresh spirit that pulses through every cobblestone. The city feels alive with support, celebration, and above all, community.

I stayed with my brother in a beautiful converted church. You know the kind, with a stoop out front, beautiful flowers and pots along the street, passersby greeting each other like neighbors even if they’ve never met. It was the perfect home base. My brother and I would go out in the mornings in the neighborhood for coffee and a pastry (bring on the pounds), and we’d sit and watch the world go by. Sometimes we’d sit at a nearby cafe for hours, watching couples and trying to figure out if it was a first date, a business meeting, or friends getting together on a beautiful day.

Pride Parade Day — The Big Event

Now let’s talk about the crown jewel of the week: the Boston Pride Parade.

The energy was absolutely electric. Picture thousands of people of every age, gender, background, and style imaginable, all marching (and dancing) through the city with music blasting and banners waving. We got there early to claim a good spot right on the stoop in front of the house (I stood on the sidewalk because I wanted to be even closer to the parade). Pro tip: bring an umbrella (we stood out in the drizzling rain), a folding stool or blanket for the steps so you are comfortable, and you’ll be set for the day.

We had front-row seats to the magic: high school groups, corporate marchers, decked out with drag queens, even the major sports teams like the Red Sox and Patriots, and so many local organizations showing up for the LGBTQIA+ community. From healthcare workers to churches to tiny family-owned businesses, everyone came out in support, all led by the Mayor of Boston and the Governor of the state.

We were decked out, too! I had my big pride earrings, t-shirt, and even shoe laces and added beads, rainbow sunglasses, pins, the works as the parade went by, all from The SWAG that was passed out.

Yes, The Swag Game Was Strong

You’ve never seen swag until you’ve been to a Pride parade in Boston. We’re talking temporary tattoos, stickers, reusable tote bags, perfume samples, keychains, beads, sunglasses, flags, and more buttons than a craft store. I came home with a collection that would make any maximalist proud.

Luckily, I came prepared. I had brought along the Lobster Pound Beverage Bucket Bag from Sea Bags — which, let me just say, is the bag for a day like this. Originally, it was packed full of snacks for the day (more on that in a second), but as the brownies and water disappeared and the bars got devoured, the bag became a catch-all for every bit of swag I snagged.

And believe me — I snagged a lot.

The bag itself got plenty of compliments, too. It’s got that nautical New England look, but it’s made from recycled sails, so it’s durable and eco-friendly. Plus, it stands upright on its own, so it was easy to plop down next to me on the sidewalk and toss in all my newfound treasures. By the end of the parade, it was stuffed full with all sorts of rainbow flags.

Treats for the Parade (and the Soul)

Before I even got to Boston, I knew I wanted to bring a little taste of sweetness with me — something to share, something indulgent, something that was perfect for Boston. I had a box of gourmet goodies from Lexington Bakes that the brand had offered to me mailed ahead, and oh my stars, they were a hit.

I tucked them carefully into my Sea Bags tote so they’d be ready when parade day came around. We had raspberry crumble oat bars, cookies with big chocolate chips, chewy salted (fleur de sel) brownies, and my favorite Cosmic Forest Cookes that are dairy free (this lactose intolerant ally thanks you) that tasted like they were baked by your favorite aunt, if your aunt had baked with real, organic fair trade ingredients. Think chewy on the inside and crisp on the outside PERFECTION.

As the floats passed and the cheers roared, we passed the cookies around. Strangers became friends over shared bites. “Where’d you get these?” someone asked with a full mouth and wide eyes. I just smiled and pointed to the box. “Lexington Bakes, they’re queer owned and make magic.”

By the time the last float passed and the drag queen baton twirlers waved goodbye, the only thing left of the snacks were a few crumbs and some chocolate smudges. But my bag? Now that was heavy — in the best way.

Exploring the City Between Celebrations

When we weren’t parade-side, we explored the city, soaking in the best of Boston. We went shopping on Newberry Street, visited the MFA and Isabelle Gardner Museum, and grabbed brunch at local LGBTQ-friendly cafés where the avocado toast was perfect and the cortados were perfection.

We checked out a show at the A.R.T., and were supposed to go listen to live music, but that was cancelled. But, really, it didn’t matter where we were, since the entire week felt like a warm hug. People were smiling more. Conversations were easier. It was one of those rare moments where it felt like everyone had collectively agreed to be kind, open, and present.

Little Moments That Made It Special

Honestly, the best parts of the trip weren’t always the loudest. They were in the quiet, connective moments. Sitting with my brother and brother-in-law over dinner, walking around the Fenway watching the family of geese, and hearing laughter bubble up from down the block.

One night, we were invited to a little rooftop get-together before we went out to the theater, and I met someone who not only grew up in the same city as I did, but had just traveled on the same cruise ship. We watched the sunset paint the skyline pink and orange while people enjoyed a glass of wine.

At 71, I’ve learned to savor these kinds of moments. They’re the real reason I came. The parade was stunning, the cookies were divine, the swag was fabulous, but it’s the people (including my brother, brother-in-law, and cousin) that made it magical.

Coming Home Full (In Every Way)

As I zipped up my Rodeo Drive carry-on to head back home to Florida, I couldn’t believe how much had happened in just one week. My bag was heavier (thank you, swag), my heart was fuller, and my faith in the goodness of community had been completely renewed.

I didn’t just go to Boston to celebrate Pride. I went to remember what it feels like to be in a space where everyone is welcome, where differences are celebrated, and where joy isn’t something you have to earn — it’s something you share.

If you’re ever wondering whether a trip like this is “worth it” yes. A thousand times, yes. Whether you’re 17 or 70, Pride in Boston is for everyone. And with the right carry-on, the right snacks, and the right bag to haul your treasures, you’ll be more than ready for the adventure.

And don’t worry — I’ll see you on that stoop again next year. I’ll bring the brownies.