How to Run a Great Local Events Newsletter

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When married couple Jonathan DeRuiter and Melissa Rutherfoord moved to Evanston, Illinois, in 2023, they kept stumbling into events they hadn’t seen listed anywhere else. “We’d be walking out to go get dinner and there’d be something going on, we’re like, ‘How the hell am I supposed to know about this?’” DeRuiter said. “It was almost like doing a research project trying to figure out what’s going on around town.”

So DeRuiter and Rutherfoord decided they needed to start a newsletter.

There are lots of local newsletter success stories, but Around Evanston is part of an emerging group of local newsletters built around one thing: Highlighting events in their community.

DeRuiter and Rutherfoord didn’t know that many people when they first moved to town. They began sending their newsletter, Around Evanston, to a grand total of seven people.

Nearly 4,400 people now get their newsletter every week.

“What we’re trying to do with a newsletter is help people connect, and we think events are a great way to do that,” DeRuiter said. “Someone recently messaged us saying they’ve lived here for nine years or something like this, and this is the first publication that made them feel that Evanston is not this sleepy little town with nothing going on.”

Why events are a great fit for newsletters

Newsletters built around curation can attract a wide audience. But these events newsletters take an interesting approach. Instead of reporting on all of the news happening in a local area, they’ve narrowed in on a specific problem: In many areas, it’s hard to find out, at a glance, what’s happening in your community.

These newsletters can also be as broad or specific as you want them to be. You could build an events newsletter that helps parents find fun stuff to do with their kids. You could create a newsletter for young people looking for low-cost events in their area. You could launch a newsletter aimed at curating just concerts or theater in your community.

Take two examples from New York City. The Skint, one of the first to publish a local events newsletter, focuses on free and cheap events in the city. W42St also has a local events newsletter, but they’re focused on events in Hell’s Kitchen. They’re two events newsletters in the same city — but with very different areas of focus. 

These events newsletters work for other reasons, too. While some newsletters struggle to explain their value to readers, this type of newsletter’s value is easy to understand: We’ll help you find fun local stuff to do and make sure you never miss out on something interesting that’s happening nearby.

There are a number of monetization opportunities with these newsletters, from ads to memberships, which means even a small list can drive significant revenue.

And these newsletters have a built-in, straightforward format: Event, date, location, cost, short description. Photos or formatting aren’t necessary. (The Skint’s built a massive list and doesn’t even use capitalization in their emails.)

Whether you work in a newsroom that could benefit from capturing the audience with an events newsletter or you simply live in an area where you see an untapped market for such a resource, here are some best practices and lessons for an events newsletter.

Figure out your angle

If you live in a major metropolitan area, your community likely has a general email events calendar, possibly even distributed by the city itself. So what will make your events newsletter worth subscribing to? The price of events? Geographical diversity (or specificity)? A particular audience? That’s more important than just being a clearinghouse of information. 

Stuart Schuffman has been covering San Francisco culture for over 20 years. Readers subscribe to his newsletter, Broke-Ass Stuart, to find inexpensive events in an expensive town, as well as his decades of being a San Francisco chronicler. “I think that it’s a great way to be a part of your community and to help people,” he said. He’s not the only newsletter about cheap events in town, but his point of view and focus on the live music scene are what set him apart from the competition. 

Cheapskate London, founded in 2019, benefits from being early on the scene of covering inexpensive events. They only feature two events per weekday — even if there are slim pickings on a Monday and lots of fun, free events on a weekend. “I find it really hard not to include them all,” cofounder Kate Samuelson said, “but I do want it to feel like it’s really handpicked and curated and thought has gone into just showcasing the very best free events.” 

Over time, they’ve figured out what they want to make space for and what they want to leave out. Easy to cut: events that are difficult for their readers to attend, like offerings on weekday afternoons when most people work. Easy to include: events that people aren’t necessarily hearing about everywhere else, especially ones in less-frequented parts of town. “[We want to include] ones that might focus on underserved communities, or are run by small community projects, or in an event space that is run by some sort of small business,” Samuelson said. “We really want to support smaller businesses, but also help people discover amazing hidden gems in London and not promote the obvious thing.”

Moreover, there’s an authenticity to Cheapskate London’s listings that keeps people reading. “We’re just the three of us,” Samuelson said of herself, cofounder Georgia Weisz, and writer Clementine Scott. “What you see is what you get. People really like that it feels like there’s a real human touch to it, because we’re not part of a big media company. I think that helps us stand out — the fact that we’re responsive and we’re just us.”

Sometimes an events newsletter editor just needs to know what the publication will and won’t include. DeRuiter and Rutherfoord of Around Evanston have simple rules for what to include in their newsletter. “It’s a combination of what we think is interesting and what we have seen performs well,” DeRuiter said. “And also, we like to reward people for reaching out to us and submitting events to us. Say we’re on the fence about something, but somebody submitted it to us, we’re much more likely to include it.” Everything they list must take place within Evanston proper, and they won’t include anything religious or political. 

Get creative with growth

One advantage of an events newsletter is that it’s fairly easy to promote to the audience. Great newsletters can explain, often in just a sentence:

• What readers will get and when they’ll get it.
• Who this newsletter is for.
• Why it’s going to be valuable for them.

The pitch for The Skint, for instance, is simple: “You don’t need to be rich to enjoy the best of the city.” Sign up, and they’ll send you a daily email with free and cheap stuff to do in New York.

Plenty of newsletters lean into a simple pitch like that. Take Catskill Crew, which has used this straightforward messaging that identifies the problem and highlights their newsletter as a solution: “Struggling to find things to do in the Catskills? Catskill Crew sends you a weekly newsletter with the best events.”

But beyond building a good message for a landing page, there are other ways to grow a newsletter like this. Cheapskate London’s leaned into a referral program: Refer one friend to the newsletter, and you’ll be entered to win a giveaway, often for tickets to a local event. “That’s been an organic, free way for us to grow,” Samuelson said. It’s a simple tactic that encourages word-of-mouth sharing.

Over the last two years, they’ve also invested in a Meta campaign, their most effective growth strategy to date. “We’ve got quite a successful Meta advert that got quite a low CPA,” or cost per acquisition, Samuelson said. “We find that’s the most cost-efficient way of getting new subscribers, but we’re going to experiment a bit with that and different ads.” The Inbox Collective team has seen similar results with their ad testing. While many publishers pay at least $1-2 to acquire a single new email address, some event-focused ads have brought in engaged subscribers for less than a dollar.

These newsletters can also pair nicely with a social media strategy. Take Salt & Seek, a Salt Lake City-based operation covering local food and events. Every week on their Instagram account, they’re highlighting the best restaurants and dishes they’ve tried recently. When you follow them, you’ll receive a direct message a few minutes later asking if you’d like to subscribe to their newsletter. (Tools like ManyChat can automate the process of sending a DM to new followers on channels like Instagram or TikTok.) They even offer new readers a $15 gift card if they sign up.

The potential audience size depends on the size of the city you cover. Schuffman originally began publishing Broke-Ass Stuart as a zine (remember those?), which turned into a blog in the mid-aughts, then an email newsletter around 2010. In a big city like San Francisco, he’s got plenty of readers to reach. Every edition of his events newsletter goes out to 35,000 readers. Cheapskate London has 61,000 subscribers at the moment, and they want to hit 100,000 by the end of 2026. “I think that’s definitely possible,” Samuelson said. “Maybe I need to aim higher considering how much we’ve grown this year, but that feels like quite a nice target.”

Try different monetization tactics

These events newsletters can be monetized in several different ways. An obvious one is ads. Around Evanston, Broke-Ass Stuart, and Cheapskate London all sell ads within the newsletter where a sponsor can promote an upcoming event or a relevant product. Some newsletters might have both featured ad listings (where you’d charge a premium rate) and a section with a handful of sponsored events (think: a classifieds-type section) below that. These ads can also be packaged with ads on social media or other platforms; Broke-Ass Stuart, for instance, sends the weekly events newsletter out to 2,000 readers via SMS.

Some newsletters, like The Skint, will also allow advertisers to send a sponsored email to their list, also known as a dedicated send. Newsletters typically charge thousands of dollars for a single dedicated send.

Both Broke-Ass Stuart and Cheapskate London have experimented with membership models. Shuffman credits his membership with keeping Broke-Ass Stuart alive during the pandemic. “It was a real earnest call: ‘Hey guys, I’ve been leading you for a decade and a half now. We need your help. We’re not going to survive this without you.’ And then it grew,” Shuffman said. Donors can receive rewards like snail-mail postcards, restaurant discounts, and free newsletter ads, depending on their membership tier. As of this writing, the Broke-Ass Stuart Patreon has nearly 1,300 members who contribute more than $4,500 per month.

Cheapskate London launched their Cheapskate Club. For £5 per month or £50 per year — the equivalent of about $6.70 or $67 — members are automatically entered into all of their weekly giveaways, plus a monthly exclusive drawing.

There are other opportunities to monetize, too. Broke-Ass Stuart offers a store where you can buy branded merch like shirts or hats. He’s experimented with coupon books, offering discounts or buy-one-get-one-free offers at Bay Area establishments. (These books typically sell for anywhere from $20 to $50.) Salt & Seek’s launched their Secret Deals Club, a membership that gets users access to an app with exclusive offers. Membership costs $10 per month.

Some events newsletters even launch their own events, like happy hours or small dinners. Catskill Crew created the Dinner Club, where readers can get matched for dinner with five strangers. You pay $16 per ticket to book your seat — not including the cost of the meal. St. Louis Magazine launched a Supper Club, where locals can enjoy a five-course menu. Tickets start at $130 — and as a twist, you don’t know who you’re dining with or where until the day of the dinner.

Pick your send date carefully

Choose how often and when you send your events newsletter based on what will be most useful to your readers, but also on your own workload and ability. Around Evanston goes out on Mondays and Thursdays, which means that Rutherfoord spends her Sunday mornings scouring sites for listings. She also finds herself revisiting her social media feed a few times since the algorithm may not surface events in a timely manner. 

Even though she and DeRuiter built tools to scrape event websites and speed up the process of finding upcoming events, creating the list still takes three hours, they estimate. After that comes the hour-plus of proofreading, since the different sources of events may utilize disparate formats, as well as confirming that the events have the right dates, links and information. 

“It’s high attention to detail. People are not going to trust it if links are wrong,” DeRuiter said. “The main thing is consistency. I mean, that’s the hard thing. We’ve been doing this for over a year, and we’ve never missed an issue whether we’re sick or traveling.”

Cheapskate London sends at the start of the week at 7:20 a.m. to give readers a chance to plan their weeks and to give them something fun to read on otherwise blah Monday mornings. “Part of the joy of Cheapskate is that everything is available that week,” Samuelson said. “It’s hard in London to be spontaneous: sometimes things get booked up, and it’s a bit of a joke here that if you want to have dinner with someone you need to plan it months in advance.” 

She finishes as much work as possible on Fridays and confirms everything is still available on Sundays. “Sometimes that can be a bit annoying having to replace things at the last minute.” But taking the extra time is part of what sets Cheapskate apart from other newsletters. “It’s really important to me that when people open the email, it’s not like, ‘Oh, sold out, sold out.’” She said this reliability is another differentiator between Cheapskate and its competitors, although to be safe, they include a disclaimer encouraging readers to double-check availability themselves.

My own newsletter, Raising Evanston, covers local news and events for parents. At first, I sent it on Tuesdays to give readers time to plan their weekend, but I found that, non-optimally, I was working on the weekends to have it ready on time. That didn’t work for me — ironically, this family newsletter was keeping me away from my own family— so we moved it to Wednesdays. Plus, this way, I benefit from grabbing any related events that might have gone out in Around Evanston’s Monday list of events (I give them credit and a link), and add any extras I may have discovered from my own research.

It’s OK to build these events into another newsletter

While the newsletter operators we spoke to have built up dedicated emails around events, others choose to include events within another newsletter offering. Some, like New England-based Daybreak, send a bonus edition of their daily newsletter every week that’s focused just on events. Others, like City Cast’s Salt Lake newsletter, incorporate an events section into every newsletter, highlighting a handful of events happening in the next 48 hours.

That strategy can make sense from a growth perspective. Daily newsletters that feature events can still promote themselves as a go-to place to find out what’s happening locally. Readers might show up looking for things to do but stick around for local news. And there are revenue opportunities here, too. Axios Charlotte, for instance, charges $300 to have a single event promoted both in their daily newsletter and on their website. City Cast Salt Lake has a regular sponsor for their “What To Do” section. KC Daily incorporates sponsored listings within their list of events.

(Full transparency: A few newsletters listed in this story, including those from Daybreak, St. Louis Magazine, and W42St, are longtime Inbox Collective clients.)

Build community around your newsletter

Much of the success of these newsletters is about making sure you’re really listening to your readers. “We get so many emails in response to our newsletter, and we reply to everyone,” Samuelson said. “We’re always asking people about stuff they want to see in the newsletter, things they like, things they don’t like, and we really go through it as a team and we’ll implement changes.” 

If you do create a newsletter like this, prepare for it to lead to some unexpected opportunities. “I like being locally famous,” said Schuffman, a onetime mayoral candidate who was honored with his own official day in San Francisco in the fall of 2025. “I live a great life. I don’t make a lot of money, but I’ve got an immense amount of perks,” in the form of free tickets to events and invitations to try out different restaurants.

DeRuiter and Rutherfoord found that with Around Evanston, they went from being new in town to being local fixtures, especially thanks to their presence at and help marketing various local fests. “One of the biggest benefits of the newsletter has been meeting people and all the relationships that we’ve built. If we didn’t start the newsletter, we’d probably know our neighbors and that’s about it,” DeRuiter said.

This sentiment is especially valuable in 2026. “If you went to Reddit, you would think everyone’s a jerk,” DeRuiter said.” We don’t see each other as humans, as individuals, and especially online. Just go out, meet your neighbors — they’re nicer and more welcoming than you might think if you spend all your time online reading comments sections.”

Five key takeaways for an events newsletter

1.) Pick a clear lane for your newsletter — You don’t need to make a newsletter that’s for everyone in your community. In fact, it might be better if you niche down. Maybe yours can focus on deals, nightlife, food, or a particular demographic. That focus can help you identify the right readers, the right advertisers to partner with, and the right content to highlight within the newsletter. When readers open the newsletter, they’ll say, “It feels like this email was written just for me!”

2.) Start small and ramp up as you grow — A newsletter like The Skint used to go out twice a week. But with a large audience, lots of advertisers, and tons of stuff happening in a city like New York, they’ve started sending their newsletter daily. Be willing to start with fewer sends — maybe once a week to start, add more when the audience and revenue demands it. 

3.) Try to monetize in multiple ways — Ads are a logical fit for many newsletters, but maybe you’ll want to try a secondary revenue stream, too. You could partner with local restaurants to sell a discount card, create a membership strategy, or host your own events. Even a newsletter with just a few hundred subscribers might be able to get a group of 5-10 out for a private dinner at a local restaurant.

4.) Keep the design simple — These newsletters don’t need to have lots of design, but they do need some sort of structure. Do you want to organize events based on the day of the week? The neighborhood they’re being hosted in? The type of event? And decide what you want to include in every event listing. Some newsletters include a simple description, a location, and a date. Others include a few sentences about the event. The format is really up to you, but pick a style (or better yet, create a style guide as a reference) so your readers enjoy a consistent, professional product. 

5.) Think about ways to expand — These newsletters offer lots of room for expansion. Cheapskate London launched an occasional newsletter for parents, called Cheapskate Kids, and a sister publication in Los Angeles called Cheapskate L.A. Going more niche or moving into other cities based on the strategies you’re already employing — both are potential opportunities for a growing events newsletter.